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Synthesis 2010(17): 2884-2892  
DOI: 10.1055/s-0030-1258184
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium(I)-Catalyzed Hydroacylation/Cycloisomerization Cascade Reaction: Application to the Construction of the Tricyclic Core of Guanacastepenes

Yoshihiro Oonishi, Ai Taniuchi, Yoshihiro Sato*
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Fax: +81(11)7064982; e-Mail: biyo@pharm.hokudai.ac.jp;
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Publikationsverlauf

Received 23 April 2010
Publikationsdatum:
16. Juli 2010 (online)

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Abstract

We previously developed a novel rhodium(I)-catalyzed cascade reaction involving the hydroacylation of a 4,6-dienal followed by cycloisomerization of the resulting 1,3-diene with an alkene, giving carbocycles containing a bicyclo[5.3.0]decenone skeleton in a stereoselective manner. Herein, we report the construction of the C5,C7,C6-tricyclic core of guanacastepenes using this cascade reaction.

Key words

rhodium - cascade reactions - dienes - aldehydes - guanacastepenes

    References

  • 1 For a review, see: Willis MC. Chem. Rev.  2010,  110:  725 ; and references cited therein
    Suche in Google Scholar
  • For reports on the construction of five-membered ring compounds via rhodium(I)-catalyzed hydroacylation, see:
  • 2a Lochow CF. Miller RG. J. Am. Chem. Soc.  1976,  98:  1281 
    Suche in Google Scholar
  • 2b Larock RC. Oertle K. Potter GF. J. Am. Chem. Soc.  1980,  102:  190 
    Suche in Google Scholar
  • 2c Sakai K. Ishiguro Y. Funakoshi K. Ueno K. Suemune H. Tetrahedron Lett.  1984,  25:  961 
    Suche in Google Scholar
  • 2d Fairlie DP. Bosnich B. Organometallics  1988,  7:  936 
    Suche in Google Scholar
  • For reports on the rhodium(I)-catalyzed asymmetric intramolecular hydroacylation of pent-4-enals, see:
  • 2e James BR. Young CG. J. Chem. Soc., Chem. Commun.  1983,  1215 
  • 2f James BR. Young CG. J. Organomet. Chem.  1985,  285:  321 
    Suche in Google Scholar
  • 2g Taura Y. Tanaka M. Funakoshi K. Sakai K. Tetrahedron Lett.  1989,  30:  6349 
    Suche in Google Scholar
  • 2h Tanaka M. Imai M. Fujio M. Sakamoto E. Takahashi M. Eto-Kato Y. Wu XM. Funakoshi K. Sakai K. Suemune H. J. Org. Chem.  2000,  65:  5806 
    Suche in Google Scholar
  • 2i Tanaka M. Sakai K. Suemune H. Curr. Org. Chem.  2003,  7:  353 
    Suche in Google Scholar
  • 2j Barnhart RW. Wang X. Noheda P. Bergens SH. Whelan J. Bosnich B. J. Am. Chem. Soc.  1994,  116:  1821 
    Suche in Google Scholar
  • 2k Bosnich B. Acc. Chem. Res.  1998,  31:  667 
    Suche in Google Scholar
  • 2l Kundu K. McCullagh JV. Morehead AT. J. Am. Chem. Soc.  2005,  127:  16042 
    Suche in Google Scholar
  • For other reports on rhodium(I)-catalyzed intramolecular hydroacylations of alkenals constructing cyclic compounds larger than five-membered rings, see:
  • 2m Gable KP. Benz GA. Tetrahedron Lett.  1991,  32:  3473 
    Suche in Google Scholar
  • 2n Bendorf HD. Colella CM. Dixon EC. Marchetti M. Matukonis AN. Musselman JD. Tiley TA. Tetrahedron Lett.  2002,  43:  7031 
    Suche in Google Scholar
  • 2o Aïssa C. Fürstner A. J. Am. Chem. Soc.  2007,  129:  14836 
    Suche in Google Scholar
  • 2p Coulter MM. Dornan PK. Dong VM. J. Am. Chem. Soc.  2009,  131:  6932 
    Suche in Google Scholar
  • 2q Aloise AD. Layton ME. Shair MD. J. Am. Chem. Soc.  2000,  122:  12610 
    Suche in Google Scholar
  • 2r Crépin D. Dawick J. Aïssa C. Angew. Chem. Int. Ed.  2009,  49:  620 
    Suche in Google Scholar
  • 3a Sato Y. Oonishi Y. Mori M. Angew. Chem. Int. Ed.  2002,  41:  1218 
    Suche in Google Scholar
  • 3b Oonishi Y. Mori M. Sato Y. Synthesis  2007,  2323 
  • 4a Sato Y. Oonishi Y. Mori M. Organometallics  2003,  22:  30 
    Suche in Google Scholar
  • 4b Oonishi Y. Saito A. Mori M. Sato Y. Synthesis  2009,  969 
  • For the cycloisomerization of 1,3-dienes with alkenes, only iron-catalyzed reactions have been reported so far by Takacs, see:
  • 5a Takacs JM. Anderson LG. J. Am. Chem. Soc.  1987,  109:  2200 
    Suche in Google Scholar
  • 5b Takacs JM. Anderson LG. Creswell MW. Takacs BE. Tetrahedron Lett.  1987,  28:  5627 
    Suche in Google Scholar
  • 5c Takacs JM. Newsome PW. Kuehn C. Tetrahedron  1990,  46:  5507 
    Suche in Google Scholar
  • 5d Takacs BE. Takacs JM. Tetrahedron Lett.  1990,  31:  2865 
    Suche in Google Scholar
  • 5e Takacs JM. Myoung YC. Tetrahedron Lett.  1992,  33:  317 
    Suche in Google Scholar
  • Other related rhodium(I)-catalyzed cycloadditions between 1,3-dienes and tethered alkenes have been reported; for [4+2] cycloadditions, see:
  • 5f Jolly RS. Luedtke G. Sheehan D. Livinghouse T. J. Am. Chem. Soc.  1990,  112:  4965 
    Suche in Google Scholar
  • 5g O’Mahony DJR. Belanger DB. Livinghouse T. Org. Biomol. Chem.  2003,  1:  2038 ; and references cited therein
    Suche in Google Scholar
  • 5h Gilbertson SR. Hoge GS. Tetrahedron Lett.  1998,  39:  2075 
    Suche in Google Scholar
  • 5i Gilbertson SR. Hoge GS. Genov DG. J. Org. Chem.  1998,  63:  10077 
    Suche in Google Scholar
  • For [2+2+1] cyclo-additions, see:
  • 5j Wender PA. Croatt MP. Deschamps NM. J. Am. Chem. Soc.  2004,  126:  5948 
    Suche in Google Scholar
  • For [2+2+2] cycloadditions, see:
  • 5k Wender PA. Christy JP. J. Am. Chem. Soc.  2006,  128:  5354 ; and references cited therein
    Suche in Google Scholar
  • 6a Trost BM. Acc. Chem. Res.  2002,  35:  695 
    Suche in Google Scholar
  • 6b Trost BM. Science  1991,  254:  1471 
    Suche in Google Scholar
  • For reviews on cascade reactions, see:
  • 7a Wasilke J.-C. Obrey SJ. Baker RT. Bazan GC. Chem. Rev.  2005,  105:  1001 
    Suche in Google Scholar
  • 7b Poli G. Giambastiani G. Heumann A. Tetrahedron  2000,  56:  5959 
    Suche in Google Scholar
  • 7c Tietze LF. Chem. Rev.  1996,  96:  115 
    Suche in Google Scholar
  • 7d Denmark SE. Thorarensen A. Chem. Rev.  1996,  96:  137 
    Suche in Google Scholar
  • 7e Winkler JD. Chem. Rev.  1996,  96:  167 
    Suche in Google Scholar
  • 7f Malacria M. Chem. Rev.  1996,  96:  289 
    Suche in Google Scholar
  • 8 Oonishi Y. Taniuchi A. Mori M. Sato Y. Tetrahedron Lett.  2006,  46:  5617 
    Suche in Google Scholar
  • 9a Brady SF. Singh MP. Janso JE. Clardy J. J. Am. Chem. Soc.  2000,  122:  2116 
    Suche in Google Scholar
  • 9b Brady SF. Bondi SM. Clardy J. J. Am. Chem. Soc.  2001,  123:  9900 
    Suche in Google Scholar
  • 10 Singh MP. Janso JE. Luckman SW. Brady SF. Clardy J. Greenstein M. Maiese WM. J. Antibiot.  2000,  53:  256 
    CrossrefSuche in Google Scholar
  • For reviews on the total syntheses of guanacastepenes and related diterpenes, see:
  • 11a Hiersemann M. Nachr. Chem.  2006,  54:  29 
    Suche in Google Scholar
  • 11b Hiersemann M. Helmboldt H. Top. Curr. Chem.  2005,  243:  73 
    Suche in Google Scholar
  • 11c Maifeld SV. Lee D. Synlett  2006,  1623 
  • 11d Mischne M. Curr. Org. Synth.  2005,  2:  261 
    Suche in Google Scholar
  • For reports on the total and formal syntheses of guanacastepenes, see:
  • 12a Tan DS. Dudley GB. Danishefsky SJ. Angew. Chem. Int. Ed.  2002,  41:  2185 
    Suche in Google Scholar
  • 12b Lin SN. Dudley GB. Tan DS. Danishefsky SJ. Angew. Chem. Int. Ed.  2002,  41:  2188 
    Suche in Google Scholar
  • 12c Mandal M. Yun HD. Dudley GB. Lin SN. Tan DS. Danishefsky SJ. J. Org. Chem.  2005,  70:  10619 
    Suche in Google Scholar
  • 12d Shi B. Hawryluk NA. Snider BB. J. Org. Chem.  2003,  68:  1030 
    Suche in Google Scholar
  • 12e Boyer FD. Hanna I. Ricard L. Org. Lett.  2004,  6:  1817 
    Suche in Google Scholar
  • 12f Mehta G. Pallavi K. Umarye JD. Chem. Commun.  2005,  4456 
  • 12g Shipe WD. Sorensen EJ.
    J. Am. Chem. Soc.  2006,  128:  7025 
    Suche in Google Scholar
  • 12h Iimura S. Overman LE. Paulini R. Zakarian A. J. Am. Chem. Soc.  2006,  128:  13095 
    Suche in Google Scholar
  • 12i Magnus P. Waring MJ. Ollivier C. Lynch V. Tetrahedron Lett.  2001,  42:  4947 
    Suche in Google Scholar
  • 12j Magnus P. Ollivier C. Tetrahedron Lett.  2002,  43:  9605 
    Suche in Google Scholar
  • 12k Nguyen TM. Lee D. Tetrahedron Lett.  2002,  43:  4033 
    Suche in Google Scholar
  • 12l Nguyen TM. Seifert RJ. Mowrey DR. Lee DS. Org. Lett.  2002,  4:  3959 
    Suche in Google Scholar
  • 12m Nakazaki A. Sharma U. Tius MA. Org. Lett.  2002,  4:  3363 
    Suche in Google Scholar
  • 12n Du XH. Chu HFV. Kwon O. Org. Lett.  2003,  5:  1923 
    Suche in Google Scholar
  • 12o Du XH. Chu HFV. Kwon OY. Tetrahedron Lett.  2004,  45:  8843 
    Suche in Google Scholar
  • 12p Srikrishna A. Dethe DH. Org. Lett.  2004,  6:  165 
    Suche in Google Scholar
  • 12q Chiu P. Li SL. Org. Lett.  2004,  6:  613 
    Suche in Google Scholar
  • For reports on synthetic studies of guanacastepenes, see:
  • 13a Dudley GB. Danishefsky SJ. Org. Lett.  2001,  3:  2399 
    Suche in Google Scholar
  • 13b Dudley GB. Tan DS. Kim G. Tanski JM. Danishefsky SJ. Tetrahedron Lett.  2001,  42:  6789 
    Suche in Google Scholar
  • 13c Dudley GB. Danishefsky SJ. Sukenick G. Tetrahedron Lett.  2002,  43:  560 
    Suche in Google Scholar
  • 13d Mandal M. Danishefsky SJ. Tetrahedron Lett.  2004,  45:  3827 
    Suche in Google Scholar
  • 13e Mandal M. Danishefsky SJ. Tetrahedron Lett.  2004,  45:  3831 
    Suche in Google Scholar
  • 13f Yun HD. Meng ZY. Danishefsky SJ. Heterocycles  2005,  66:  711 
    Suche in Google Scholar
  • 13g Yun HD. Danishefsky SJ. Tetrahedron Lett.  2005,  46:  3879 
    Suche in Google Scholar
  • 13h Cheong PHY. Yun H. Danishefsky SJ. Houk KN. Org. Lett.  2006,  8:  1513 
    Suche in Google Scholar
  • 13i Snider BB. Hawryluk NA. Org. Lett.  2001,  3:  569 
    Suche in Google Scholar
  • 13j Snider BB. Shi B. Tetrahedron Lett.  2001,  42:  9123 
    Suche in Google Scholar
  • 13k Boyer FD. Hanna I. Tetrahedron Lett.  2002,  43:  7469 
    Suche in Google Scholar
  • 13l Boyer FD. Hanna I. J. Org. Chem.  2005,  70:  1077 
    Suche in Google Scholar
  • 13m Mehta G. Umarye JD. Org. Lett.  2002,  4:  1063 
    Suche in Google Scholar
  • 13n Mehta G. Umarye JD. Gagliardini V. Tetrahedron Lett.  2002,  43:  6975 
    Suche in Google Scholar
  • 13o Mehta G. Umarye JD. Srinivas K. Tetrahedron Lett.  2003,  44:  4233 
    Suche in Google Scholar
  • 13p Mehta G. Umarye JD. Tetrahedron Lett.  2003,  44:  7285 
    Suche in Google Scholar
  • 13q Shipe WD. Sorensen EJ. Org. Lett.  2002,  4:  2063 
    Suche in Google Scholar
  • 13r Brummond KM. Gao D. Org. Lett.  2003,  5:  3491 
    Suche in Google Scholar
  • 13s Sarpong R. Su JT. Stoltz BM. J. Am. Chem. Soc.  2003,  125:  13624 
    Suche in Google Scholar
  • 13t Li CC. Liang S. Zhang XH. Xie ZX. Chen JH. Wu YD. Yang Z. Org. Lett.  2005,  7:  3709 
    Suche in Google Scholar
  • 13u Li CC. Wang CH. Liang B. Zhang XH. Deng LJ. Liang S. Chen JH. Wu YD. Yang Z. J. Org. Chem.  2006,  71:  6892 
    Suche in Google Scholar
  • 13v Gradl SN. Kennedy-Smith JJ. Kim J. Trauner D. Synlett  2002,  411 
  • 13w Hughes CC. Kennedy-Smith JJ. Trauner D. Org. Lett.  2003,  5:  4113 
    Suche in Google Scholar
  • 13x Hughes CC. Miller AK. Trauner D. Org. Lett.  2005,  7:  3425 
    Suche in Google Scholar
  • 13y McGowan CA. Schmieder AK. Roberts L. Greaney MF. Org. Biomol. Chem.  2007,  5:  1522 
    Suche in Google Scholar
  • 13z Michalak K. Michalak M. Wicha J. Tetrahedron Lett.  2008,  49:  6807 ; and references cited therein
    Suche in Google Scholar
  • 14 Sato Y. Oonishi Y. Mori M. J. Org. Chem.  2003,  68:  9858 
    CrossrefPubMedSuche in Google Scholar
  • 15 Zoller T. Uguen D. De Cian A. Fischer J. Sablé S. Tetrahedron Lett.  1997,  38:  3409 
    CrossrefSuche in Google Scholar
  • 16 Bennacer B. Trubuil D. Rivalle C. Grierson DS. Eur. J. Org. Chem.  2003,  4561 
    Crossref