Synthetic Approaches to Naturally Occurring Ten-Membered-Ring Lactones

Helena M. C. Ferraz; Fernanda I. Bombonato; Luiz S. Longo Jr

doi:10.1055/s-2007-990831

REVIEW

Synthetic Approaches to Naturally Occurring Ten-Membered-Ring Lactones

Helena M. C. Ferraz*^a,†, Fernanda I. Bombonato^a, Luiz S. Longo Jr*^b
^a Instituto de Química, Universidade de São Paulo, CP 26077, 05513-970 São Paulo, SP, Brazil
^b Universidade Federal de São Paulo, Campus Diadema, 09972-270 Diadema, SP, Brazil
e-Mail: luiz.longo@unifesp.br;

Abstract

All articles of this category

Abstract

The strategies for the synthesis of naturally occurring ten-membered-ring lactones, which are the most abundant of the medium-ring lactones, are discussed. According to their structures and/or biosynthesis, the molecules are classified in monocyclic polyketides, monocyclic oxylipins, aliphatic bicyclic and aromatic bicyclic lactones. In each subsection, the lactones are presented in chronological order of their isolation. Representative complex systems bearing multiple functionalities in addition to the lactone moiety, as well as a selection of recent synthetic approaches to non-natural medium-ring lactones, are briefly presented.

1 Introduction

2 Monocyclic Ten-Membered-Ring Lactones

2.1 Polyketides

2.2 Oxylipins

3 Bicyclic Ten-Membered-Ring Lactones

3.1 Aliphatic

3.2 Aromatic

4 Complex Ten-Membered-Ring Lactones

5 Non-natural Lactones: Selected Synthetic Approaches

6 Conclusion

Key words

natural products - medium-sized-ring systems - ten-membered-ring lactones - monocyclic lactones - bicyclic lactones

Full Text

References

1 Back TG. Tetrahedron 1977, 33: 3041

2 Roxburgh CJ. Tetrahedron 1993, 49: 10749

3 Illuminati G. Mandolini L. Acc. Chem. Res. 1981, 14: 95

4 Wiberg KB. Waldron RF. J. Am. Chem. Soc. 1991, 113: 7697

5 Petasis NA. Patane MA. Tetrahedron 1992, 48: 5757

6 Mehta G. Singh V. Chem. Rev. 1999, 99: 881

7 Minnaard AJ. Wijnberg JBPA. de Groot A. Tetrahedron 1999, 55: 2115

8 Rousseau G. Tetrahedron 1995, 51: 2777

9 Dräger G. Kirschning A. Thiericke R. Zerlin M. Nat. Prod. Rep. 1996, 13: 365

10 Longo LS. Bombonato FI. Ferraz HMC. Quim. Nova 2007, 30: 415

11 Crimmins MT. Emmitte KA. J. Am. Chem. Soc. 2001, 123: 1533 ; and references cited therein

12 Evans PA. Holmes AB. Tetrahedron 1991, 47: 9131

13 Nubbemeyer U. Top. Curr. Chem. 2001, 216: 125

14 Yet L. Chem. Rev. 2000, 100: 2963

15 Nubbemeyer U. Eur. J. Org. Chem. 2001, 1801

16 Parenty A. Moreau X. Campagne J.-M. Chem. Rev. 2006, 106: 911

17 Gradillas A. Perez-Castells J. Angew. Chem. Int. Ed. 2006, 45: 6086

18 van der Mee L. Helmich F. de Bruijn R. Vekemans JAJM. Palmans ARA. Meijer EW. Macromolecules 2006, 39: 5021

19 Shiina I. Chem. Rev. 2007, 107: 239

20 Ishida T. Wada K. J. Chem. Soc., Chem. Commun. 1975, 209

21 Wada K. Ishida T. J. Chem. Soc., Chem. Commun. 1976, 340

22 Wada K. Ishida T. J. Chem. Soc., Perkin Trans. 1 1979, 1154

23 Farooq A. Gordon J. Hanson JR. Takahashi JA. Phytochemistry 1995, 38: 557

24 Ackland MJ. Hanson JR. Hitchcock PB. Ratcliffe AH. J. Chem Soc., Perkin Trans. 1 1985, 843

25a Ishida T. Wada K. J. Chem. Soc., Chem. Commun. 1977, 337

25b Ishida T. Wada K. J. Chem. Soc., Perkin Trans. 1 1979, 323

26a Wakamatsu T. Akasaka K. Ban Y. Tetrahedron Lett. 1977, 2755

26b Wakamatsu T. Akasaka K. Ban Y. J. Org. Chem. 1979, 44: 2008

27 Anand RV. Baktharaman S. Singh VK. J. Org. Chem. 2003, 68: 3356

28 Ireland RE. Brown FR. J. Org. Chem. 1980, 45: 1868

29 Tsuji J. Mandai T. Tetrahedron Lett. 1978, 1817

30 Shenvi AB. Gerlach H. Helv. Chim. Acta 1980, 63: 2426

31 Boeckman RK. Pruitt JR. J. Am. Chem. Soc. 1989, 111: 8286

32 Sharma GVM. Reddy KL. Tetrahedron: Asymmetry 2006, 17: 3197

33 Moore BP. Brown WV. Aust. J. Chem. 1976, 29: 1365

34 Gerlach H. Künzler P. Oertle K. Helv. Chim. Acta 1978, 61: 1226

35 Cossy J. Pete JP. Tetrahedron Lett. 1986, 27: 2369

36 Bartra M. . J. Org. Chem. 1991, 56: 5132

37 Kitahara T. Koseki K. Mori K. Agric. Biol. Chem. 1983, 47: 389

38 Naoshima Y. Hasegawa H. Nishiyama T. Nakamura A. Bull. Chem. Soc. Jpn. 1989, 62: 608

39 Jones GB. Huber RS. Chapman BJ. Tetrahedron: Asymmetry 1997, 8: 1797

40 Petrzilka M. Helv. Chim. Acta 1978, 61: 3075

41 Takahashi T. Hashiguchi S. Kasuga K. Tsuji J. J. Am. Chem. Soc. 1978, 100: 7424

42 Trost BM. Verhoeven TR. J. Am. Chem. Soc. 1980, 102: 4743

43 Malherbe R. Rist G. Bellus D. J. Org. Chem. 1983, 48: 860

44 Vedejs E. Powell DW. J. Am. Chem. Soc. 1982, 104: 2046

45 Fouque E. Rousseau G. Synthesis 1989, 661

46 Ohnuma T. Hata N. Miyachi N. Wakamatsu T. Ban Y. Tetrahedron Lett. 1986, 27: 219

47 Ballini R. Marcantoni E. Petrini M. Liebigs Ann. 1995, 1381

48 Enders D. Plant A. Drechsel K. Prokopenko OF. Liebigs Ann. 1995, 1127

49 Saikia AK. Hazarika MJ. Barua NC. Bezbarua MS. Sharma RP. Ghosh AC. Synthesis 1996, 981

50 Mahajan JR. Silva CR. J. Braz. Chem. Soc. 1990, 1: 87

51 Mahajan JR. Araujo HC. Synthesis 1981, 49

52 Kostova K. Hesse M. Helv. Chim. Acta 1984, 67: 1713

53 Stanchev S. Hesse M. Helv. Chim. Acta 1990, 73: 460

54 Suginome H. Yamada S. Tetrahedron 1987, 43: 3371

55 Ono N. Miyake H. Kaji A. J. Org. Chem. 1984, 49: 4997

56 Posner GH. Asirvatham E. Webb KS. Jew S. Tetrahedron Lett. 1987, 28: 5071

57 Posner GH. Wang Q. Halford BA. Elias JS. Maxwell JP. Tetrahedron Lett. 2000, 41: 9655

58 Hatcher MA. Borstnik K. Posner GH. Tetrahedron Lett. 2003, 44: 5407

59 Posner GH. Hatcher MA. Maio WA. Org. Lett. 2005, 7: 4301

60 Nagumo S. Suemune H. Sakai K. Tetrahedron 1992, 48: 8667

61 Nukina M. Sassa T. Ikeda M. Tetrahedron Lett. 1980, 21: 301

62 Nukina M. Ikeda M. Sassa T. Agric. Biol. Chem. 1980, 44: 2761

63 Venkatasubbaiah P. Chilton WS. J. Nat. Prod. 1992, 55: 461

64 Asaoka M. Naito S. Takei H. Tetrahedron Lett. 1985, 26: 2103

65 Moricz A. Gassmann E. Bienz S. Hesse M. Helv. Chim. Acta 1995, 78: 663

66 Suzuki S. Tanaka A. Yamashita K. Agric. Biol. Chem. 1987, 51: 3095

67 Wasserman HH. Prowse KS. Tetrahedron 1992, 48: 8199

68a Grabley S. Granzer E. Hutter K. Ludwig D. Mayer M. Thiericke R. Till G. Wink J. Phillips S. Zeeck A. J. Antibiot. 1992, 45: 56

68b Gohrt A. Zeeck A. Hutter K. Kirsch R. Kluge H. Thiericke R. J. Antibiot. 1992, 45: 66

68c Grabley S. Hammann P. Hutter K. Kirsch R. Kluge H. Thiericke R. Mayer M. Zeeck A. J. Antibiot. 1992, 45: 1176

69 Ayer WA. Sun M. Browne LM. Brinen LS. Clardy J. J. Nat. Prod. 1992, 55: 649

70 Rukachaisirikul V. Pramjit S. Pakawatchai C. Isaka M. Supothina S. J. Nat. Prod. 2004, 67: 1953

71 Boonphong S. Kittakoop P. Isaka M. Pittayakhajonwut D. Tanticharoen M. Thebtaranonth Y. J. Nat. Prod. 2001, 64: 965

72 Mayer M. Thiericke R. J. Antibiot. 1993, 46: 1372

73 Mayer M. Thiericke R. J. Chem. Soc., Perkin Trans. 1 1993, 495

74 Colle S. Taillefumier C. Chapleur Y. Liebl R. Schmidt A. Bioorg. Med. Chem. 1999, 7: 1049

75 Yamada S. Tanaka A. Oritani T. Biosci., Biotechnol., Biochem. 1995, 59: 1657

76 Arai M. Morita N. Aoyagi S. Kibayashi C. Tetrahedron Lett. 2000, 41: 1199

77 Andrus MB. Shih TL. J. Org. Chem. 1996, 61: 8780

78a Kobayashi Y. Asano M. Yoshida S. Takeuchi A. Org. Lett. 2005, 7: 1533

78b Kobayashi Y. Yoshida S. Asano M. Takeuchi A. Acharya HP. J. Org. Chem. 2007, 72: 1707

79 Krishna PR. Reddy PVN. Tetrahedron Lett. 2006, 47: 7473

80a Pilli RA. Victor MM. Tetrahedron Lett. 1998, 39: 4421

80b Pilli RA. Victor MM. J. Braz. Chem. Soc. 2001, 12: 373

81a Okude Y. Hirano S. Hiyama T. Nozaki H. J. Am. Chem. Soc. 1977, 99: 3179

81b Jin H. Uenishi J. Christ WJ. Kishi Y. J. Am. Chem. Soc. 1986, 108: 5644

82 Mohapatra DK. Ramesh DK. Giardello MA. Chorghade MS. Gurjar MK. Grubbs RH. Tetrahedron Lett. 2007, 48: 2621

83 Fuchser J. Zeeck A. Liebigs Ann./Recl. 1997, 87

84 Pilli RA. Victor MM. de Meijere A. J. Org. Chem. 2000, 65: 5910

85 For a review, see: Katz L. Chem. Rev. 1997, 97: 2557

86 Evidente A. Lanzetta R. Capasso R. Vurro M. Bottalico A. Phytochemistry 1993, 34: 999

87 Evidente A. Capasso R. Abouzeid MA. Lanzetta R. Vurro M. Bottalico A. J. Nat. Prod. 1993, 56: 1937

88 Arnone A. Assante G. Montorsi M. Nasini G. Ragg E. Gazz. Chim. Ital. 1993, 123: 71

89 Garcia-Fortanet J. Murga J. Falomir E. Carda M. Marco JA. J. Org. Chem. 2005, 70: 9822

90 Evidente A., Lanzetta R., Capasso R., Andolfi A., Bottalico A., Vurro M., Zonno M. C.; Phytochemistry; 1995, 40: 1637

91 Evidente A. Lanzetta R. Capasso R. Andolfi A. Vurro M. Zonno MC. Phytochemistry 1997, 44: 1041

92 Evidente A. Capasso R. Andolfi A. Vurro M. Zonno MC. Phytochemistry 1998, 48: 941

93 de Napoli L. Messere A. Palomba D. Piccialli V. Evidente A. Piccialli G. J. Org. Chem. 2000, 65: 3432

94 Fürstner A. Radkowski K. Wirtz C. Goddard R. Lehmann CW. Mynott R. J. Am. Chem. Soc. 2002, 124: 7061

95 Liu D. Kozmin SA. Org. Lett. 2002, 4: 3005

96 Rivero-Cruz JF. Garcia-Aguirre G. Cerda-Garcia-Rojas CM. Mata R. Tetrahedron 2000, 56: 5337

97 Rivero-Cruz JF. Garcia-Aguirre G. Cerda-Garcia-Rojas CM. Mata R. J. Nat. Prod. 2003, 66: 511

98 Fürstner A. Radkowski K. Chem. Commun. 2001, 671

99a Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Synlett 2003, 1186

99b Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Helv. Chim. Acta 2003, 86: 3717

100 Sabino AA. Pilli RA. Tetrahedron Lett. 2002, 43: 2819

101 Gurjar MK. Karmakar S. Mohapatra DK. Tetrahedron Lett. 2004, 45: 4525

102 Salaskar A. Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry 2006, 17: 325

103 Boruwa J. Gogoi N. Barua NC. Org. Biomol. Chem. 2006, 4: 3521

104 Nanda S. Tetrahedron Lett. 2005, 46: 3661

105 Ratnayake AS. Yoshida WY. Mooberry SL. Hemsheidt T. Org. Lett. 2001, 3: 3479

106 Bodo B. Molho L. Davoust D. Molho D. Phytochemistry 1983, 22: 447

107 Murga J. Falomir E. Garcia-Fortanet J. Carda M. Marco JA. Org. Lett. 2002, 4: 3447

108 Batty D. Crich D. J. Chem. Soc., Perkin Trans. 1 1992, 3193

109 Chavan SP. Praveen C. Tetrahedron Lett. 2005, 46: 1939

110 Fürstner A. Nagano T. Muller C. Seidel G. Muller O. Chem. Eur. J. 2007, 13: 1452

111 Gurjar MK. Nagaprasad R. Ramana CV. Tetrahedron Lett. 2003, 44: 2873

112 Ghosh S. Rao RV. Shashidhar J. Tetrahedron Lett. 2005, 46: 5479

113a Davoli P. Spaggiari A. Castagnetti L. Prati F. Org. Biomol. Chem. 2004, 2: 38

113b Davoli P. Fava R. Morandi S. Spaggiari A. Prati F. Tetrahedron 2005, 61: 4427

114 Sharma GVM. Cherukupalli GR. Tetrahedron: Asymmetry 2006, 17: 1981

115a Ishigami K. Kitahara T. Heterocycles 2004, 63: 785

115b Ishigami K. Watanabe H. Kitahara T. Tetrahedron 2005, 61: 7546

116 Kumar P. Naidu SVJ. J. Org. Chem. 2005, 70: 4207

117 Prasad KR. Penchalaiah K. Choudhary A. Anbarasan P. Tetrahedron Lett. 2007, 48: 309

118 Banwell MG. Loong DTJ. Heterocycles 2004, 62: 713

For reviews about oxylipins, see:

119a Gerwick WH. Chem. Rev. 1993, 93: 1807

119b Noverr MC. Erb-Downward JR. Huffnagle GB. Clin. Microbiol. Rev. 2003, 16: 517

120 Seo Y. Cho KW. Rho JR. Shin J. Kwon BM. Bok SH. Song JI. Tetrahedron 1996, 52: 10583

121 Niwa H. Wakamatsu K. Yamada K. Tetrahedron Lett. 1989, 30: 4543

122 Luo X. Li F. Hong J. Lee C.-O. Sim CJ. Im KS. Jung JH. J. Nat. Prod. 2006, 69: 567

123 Niwa H. Inagaki H. Yamada K. Tetrahedron Lett. 1991, 32: 5127

124 Niwa H. Watanabe M. Inagaki H. Yamada K. Tetrahedron 1994, 50: 7385

125 Lindquist N. Fenical W. Tetrahedron Lett. 1989, 30: 2735

126 Congrève MS. Holmes AB. Hughes AB. Looney MG. J. Am. Chem. Soc. 1993, 115: 5815

127 Fürstner A. Schlede M. Adv. Synth. Catal. 2002, 344: 657

128 Papendorf O. Konig GM. Wright AD. Chorus I. Oberemm A. J. Nat. Prod. 1997, 60: 1298

129 Stierle DB. Stierle AA. Bugni T. Loewen G. J. Nat. Prod. 1998, 61: 251

130a Ishigami K. Motoyoshi H. Kitahara T. Tetrahedron Lett. 2000, 41: 8897

130b Motoyoshi H. Ishigami K. Kitahara T. Tetrahedron 2001, 57: 3899

131 Naves YR. Grampoloff AV. Helv. Chim. Acta 1942, 25: 1500

132 Demole E. Willhalm B. Stoll M. Helv. Chim. Acta 1964, 47: 1152

133 Gerlach H. Kunzler P. Helv. Chim. Acta 1978, 61: 2503

134 Fürstner A. Muller T. Synlett 1997, 1010

135 Kitahara T. Iwamoto M. Takagi Y. Mori K. Matsui M. Agric. Biol. Chem. 1984, 48: 1731

136 Shimizu I. Nakagawa H. Tetrahedron Lett. 1992, 33: 4957

137 Inoue M. Nishi T. Kitahara T. Biosci., Biotechnol., Biochem. 1999, 63: 1122

138 Chu M. Mierzwa R. Xu L. He L. Terracciano J. Patel M. Gullo V. Black T. Zhao W. Chan T.-M. McPhail AT. J. Nat. Prod. 2003, 66: 1527

139 Jayasuriya H. Zink DL. Polishook JD. Bills GF. Dombrowski AW. Genilloud O. Pelaez FF. Herranz L. Quamina D. Lingham RB. Danzeizen R. Graham PL. Tomassini JE. Singh SB. Chemistry & Biodiversity 2005, 2: 112

140 Mehta G. Shinde HM. Chem. Commun. 2005, 3703

141 Mehta G. Shinde HM. Tetrahedron Lett. 2005, 46: 6633

142 Wilson EM. Trauner D. Org. Lett. 2007, 9: 1327

143 Ishigami K. Katsuta R. Watanabe H. Tetrahedron 2006, 62: 2224

144 Snider BB. Zhou J. Org. Lett. 2006, 8: 1283

145 Kinoshita K. Sasaki T. Awata M. Takada M. Yaginuma S. J. Antibiot. 1997, 50: 961

146 Murakami Y. Ishii A. Mizuno S. Yaginuma S. Uehara Y. Anticancer Res. 1999, 19: 4145

147 Edrada RA. Heubes M. Brauers G. Wray V. Berg A. Grafe U. Wohlfarth M. Muhlbacher J. Schaumann K. . Bringmann G. Proksch P. J. Nat. Prod. 2002, 65: 1598

148 Bringmann G. Lang G. Michel M. Heubes M. Tetrahedron Lett. 2004, 45: 2829

149 Yoshino T. Ng F. Danishefsky SJ. J. Am. Chem. Soc. 2006, 128: 14185

150 Liang Q. Zhang J. Quan W. Sun Y. She X. Pan X. J. Org. Chem. 2007, 72: 2694

151 Jansen R. Kunze B. Reichenbach H. Höfle G. Eur. J. Org. Chem. 2000, 913

152 Bhattacharjee A. Seguil OR. De Brabander JK. Tetrahedron Lett. 2001, 42: 1217

153a Nicolaou KC. Kim DW. Baati R. Angew. Chem. Int. Ed. 2002, 41: 3701

153b Nicolaou KC. Kim DW. Baati R. O’Brate A. Giannakakou P. Chem. Eur. J. 2003, 9: 6177

154 Su Q. Panek JS. J. Am. Chem. Soc. 2004, 126: 2425

155 Petri AF. Bayer A. Maier ME. Angew. Chem. Int. Ed. 2004, 43: 5821

156a Lewis A. Stefanuti I. Swain SA. Smith SA. Taylor RJK. Tetrahedron Lett. 2001, 42: 5549

156b Lewis A. Stefanuti I. Swain SA. Smith SA. Taylor RJK. Org. Biomol. Chem. 2003, 1: 104

157 Hilli F. White JM. Rizzacasa MA. Tetrahedron Lett. 2002, 43: 8507

158 Kuhnert SM. Maier ME. Org. Lett. 2002, 4: 643

159 Graetz BR. Rychnovsky SD. Org. Lett. 2003, 5: 3357

160 Hilli F. White JM. Rizzacasa MA. Org. Lett. 2004, 6: 1289

161 Li M. O’Doherty GA. Org. Lett. 2006, 8: 6087

162 Yadav JS. Kumar NN. Prasad AR. Synthesis 2007, 1175

163 Aimi N. Uchida N. Ohya N. Hosokawa H. Takayama H. Sakai S.-i. Mendonza LA. Polz L. Stockigt J. Tetrahedron Lett. 1991, 32: 4949

164a Takahashi S. Kakinuma N. Uchida K. Hashimoto R. Yanagishima T. Nakagawa A. J. Antibiot. 1998, 51: 596

164b Takahashi S. Kakinuma N. Uchida K. Hashimoto R. Yanagishima T. Nakagawa A. J. Antibiot. 1998, 51: 1051

165 Irlapati NR. Baldwin JE. Adlington RM. Pritchard GJ. Cowley AR. Tetrahedron 2006, 62: 4603

166 Celmer WD. Chmurny GN. Moppett CE. Ware RS. Watts PC. Whipple EB. J. Am. Chem. Soc. 1980, 102: 4203

167 Whaley HA. Chidester CG. Mizsak SA. Wnuk RJ. Tetrahedron Lett. 1980, 21: 3659

168a Rasmussen RR. Scherr MH. Whittern DN. Buko AM. McAlpine JB. J. Antibiot. 1987, 40: 1383

168b McAlpine JB. Mitscher LA. Jackson M. Rasmussen RR. Velde DV. Veliz E. Tetrahedron 1996, 52: 10327

169 Roush WR. Koyama K. Curtin ML. Moriarty KJ. J. Am. Chem. Soc. 1996, 118: 7502

170 Gossinger E. Schwartz A. Sereinig N. Tetrahedron 2001, 57: 3045 ; and references cited therein

171 Gossinger E. Schwartz A. Sereinig N. Tetrahedron 2000, 56: 2007 ; and references cited therein

172 Ferraz HMC. Longo LS. Org. Lett. 2003, 5: 1337

173 Ferraz HMC. Longo LS. J. Org. Chem. 2007, 72: 2945

174 Hassner A. Pradhan TK. Tetrahedron Lett. 2006, 47: 5511

175 Métay E. Léonel E. Condon S. Nédélec JY. Tetrahedron 2006, 62: 8515

176 Ishihara K. Kubota M. Kurihara H. Yamamoto H. J. Org. Chem. 1996, 61: 4560

177 Abramite JA. Sammakia T. Org. Lett. 2007, 9: 2103

178 Corey EJ. Nicolaou KC. J. Am. Chem. Soc. 1974, 96: 5614

179 Inanaga J. Hirata K. Saeki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn. 1979, 52: 1989

180 Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18