Synthesis of ent-Halimanolides from ent-Halimic Acid

I. S. Marcos; A. B. Pedrero; M. J. Sexmero; D. Diez; N. García; M. A. Escola; P. Basabe; A. Conde; R. F. Moro; J. G. Urones

doi:10.1055/s-2005-918475

PAPER

Synthesis of ent-Halimanolides from ent-Halimic Acid

I. S. Marcos*, A. B. Pedrero, M. J. Sexmero, D. Diez, N. García, M. A. Escola, P. Basabe, A. Conde, R. F. Moro, J. G. Urones
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, 37008 Salamanca, Spain
Fax: +34(923)294574; e-Mail: ismarcos@usal.es;

Abstract

All articles of this category

Abstract

Three natural ent-halimanolides have been synthesized from ent-halimic acid. Their structures have been confirmed as well as their absolute configurations established. Bestmann methodology has been used for the synthesis of butenolides and for the synthesis of γ-hydroxybutenolides the Boukouvalas method has been employed.

Key words

diterpenes - alkaloids - ent-halimanolides - reduction

Full Text

References

1 Trost BM. Calkins TL. Bochet CG. Angew. Chem. Int. Ed. 1997, 36: 2632

2 Marshall JA. Jing H. Tetrahedron Lett. 1998, 39: 1493

3 Yu J.-G. Hu XE. Ho DK. Ben MF. Stephens RE. Cassady JM. Brinen LS. Clardy J. J. Org. Chem. 1994, 59: 1598

4 Leboeuf M. Cave A. Bhaumik PK. Mukherjee B. Mukherjee R. Phytochemistry 1982, 21: 2783

5 Kijjoa A. Pinto MMM. Pinho MM. Herz W. Phytochemistry 1993, 34: 457

6a Ma X. Lee I.-S. Chai H.-B. Farsworth NR. Soejarto DD. Cordel GA. Pezzuto JM. Kinghorn AD. Phytochemistry 1994, 37: 1659

6b Hao X.-J. Yang X.-S. Zhang Z. Shang L.-J. Phytochemistry 1995, 39: 447

7 Wijerathne EMK. da Silva LB. Tezuka Y. Kikuchi T. Phytochemistry 1995, 39: 443

8 Costa M. Tanaka CMA. Imamura PM. Marsaioli AJ. Phytochemistry 1999, 50: 117

9 Yoo H.-D. Cremin PA. Zeng L. Garo E. Williams CT. Lee CM. Goering MG. O’Neil-Johnson M. Eldridge GR. Hu J.-F. J. Nat. Prod. 2005, 68: 122

10 Hara N. Asaki H. Fujimoto Y. Gupta YK. Singh AK. Sahai M. Phytochemistry 1995, 38: 189

11a Faizi S. Khan RA. Azher S. Khan SA. Tauseef S. Ahmad A. Planta Med. 2003, 69: 350

11b Okorie DA. Tetrahedron 1980, 36: 2005

11c Hasan CM. Healey TM. Waterman PG. Schwalbe CH. J. Chem. Soc., Perkin Trans. 1 1982, 2807

11d Hocquemiller R. Dubois G. Leboeuf M. Cave A. Kunesch N. Riche C. Chiaroni A. Tetrahedron Lett. 1981, 5057

12 Imamura M. Costa M. J. Nat. Prod. 2000, 63: 1623

13 Marcos IS. González JL. Sexmero MJ. Diez D. Basabe P. Williams DJ. Simmonds MSJ. Urones JG. Tetrahedron Lett. 2000, 41: 2553

14a Marcos IS. Pedrero AB. Sexmero MJ. Diez D. Basabe P. Hernández FA. Broughton HB. Urones JG. Synlett 2002, 105

14b Marcos IS. Pedrero AB. Sexmero MJ. Díez D. Basabe P. García N. Moro RF. Broughton HB. Mollinedo F. Urones JG. J. Org. Chem. 2003, 68: 7496

15a Gunasekera GP. McCarthy PJ. Kelly-Borges M. Lobkovsky E. Clardy J. J. Am. Chem. Soc. 1996, 118: 8759

15b Jung ME. Nishimura N. Org. Lett. 2001, 3: 2113

15c Brohm D. Metzger S. Bhargava A. Müller O. Lieb F. Waldmann H. Angew. Chem. Int. Ed. 2002, 41: 307

15d Brohm D. Philippe N. Metzger S. Bhargava A. Muller O. Lieb F. Waldmann H. J. Am. Chem. Soc. 2002, 124: 13171

16a Marcos IS. Hernández FA. Sexmero MJ. Diez D. Basabe P. Pedrero AB. Garcia N. Sanz F. Urones JG. Tetrahedron Lett. 2002, 43: 1243

16b Marcos IS. Hernández FA. Sexmero MJ. Diez D. Basabe P. Pedrero AB. Garcia N. Urones JG. Tetrahedron 2003, 59: 685

17a de Pascual TJ. Urones JG. Marcos IS. Bermejo F. Basabe P. Queimadelos P. An. Quim., Ser. C 1983, 79: 451

17b . J. Am. Chem. Soc. 1946, 68: 2487

17c . J. Am. Chem. Soc. 1949, 71: 3301

17d Desmaële D. Mekouar K. d’Angelo J. J. Org. Chem. 1997, 62: 3890

17e Toyota M. Wada T. Fukumoto K. Ihara M. J. Am. Chem. Soc. 1998, 120: 4916

17f Toyota M. Wada T. Ihara M. J. Org. Chem. 2000, 65: 4565

17g Hsu D.-S. Liao C.-C. Org. Lett. 2003, 5: 4741

17h Furrow ME. Myers AG. J. Am. Chem. Soc. 2004, 126: 5436

17i Bredenkötter B. Flörke U. Kuck D. Chem.-Eur. J. 2001, 7: 3387

18a Brady TP. Kim SH. Wen K. Theodorakis EA. Angew. Chem. Int. Ed. 2004, 43: 739

18b Barton DHR. McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975, 1574

18c Barton DHR. Motherwell WB. Stange A. Synthesis 1981, 743

18d Barton DHR. Parekh SI. Tse C.-L. Tetrahedron Lett. 1993, 34: 2733

18e Barton DHR. Tetrahedron 1992, 48: 2529

18f Crich D. Quintero L. Chem. Rev. 1989, 89: 1413

18g Srikrishna A. Gharpure SJ. J. Org. Chem. 2001, 66: 4379

19 Zhabinskii VN. Minnaard AJ. Wijnberg JBPA. de Groot A. J. Org. Chem. 1996, 61: 4022

20a Marcos IS. Moro RF. Carballares S. Urones JG. Tetrahedron 2001, 57: 713

20b Imuta M. Ziffer H. J. Org. Chem. 1979, 44: 1351

20c Anderson WK. Veysoglu J. J. Org. Chem. 1973, 38: 2267

20d Schröder M. Chem. Rev. 1980, 80: 187

21a Lohray BB. Tetrahedron: Asymmetry 1992, 3: 1317

21b Haines AH. In Comprehensive Organic Synthesis, Vol. 7 Trost BM. Fleming I. Pergamon Press; Oxford: 1991. p.467

21c Thomas AF. Vial C. Ozainne M. Ohloff G. Helv. Chim. Acta 1973, 56: 2270

21d Marcos IS. Moro RF. Carballares S. Urones JG. Synthesis 2000, 541

22a Ley SV. Norman J. Griffith WP. Marsden SP. Synthesis 1994, 639

22b Díez Martín D. Kotecha NR. Ley SV. Mantegani S. Menéndez JC. Organ HH. White AD. Tetrahedron 1992, 48: 7899

22c Griffith WP. Ley SV. Whitcombe GP. White AD. J. Chem. Soc., Chem. Commun. 1987, 1625

23a Thomas AF. Vial C. Ozainne M. Ohloff G. Helv. Chim. Acta 1973, 56: 2270

23b Bestmann HJ. Angew. Chem., Int. Ed. Engl. 1977, 16: 349

24a Brownbridge P. Synthesis 1983, 1

24b Corey EJ. Gross AW. Tetrahedron Lett. 1984, 25: 495

25a Rubottom GM. Gruber JM. J. Org. Chem. 1978, 43: 1599

25b Rubottom GM. Vázquez MA. Pelegrina DR. Tetrahedron Lett. 1974, 49: 4319

26 Boukovalas J. Lachance N. Synlett 1998, 31

27a Boukovalas J. Maltais F. Lachance N. Tetrahedron Lett. 1994, 35: 7897

27b Jas G. Synthesis 1991, 965

27c Martin SF. Barr KJ. J. Am. Chem. Soc. 1996, 118: 3299

28 Urones JG. de Pascual Teresa J. Marcos IS. Diez D. Garrido NM. Guerra RA. Phytochemistry 1987, 26: 1077 ; and references cited therein