Stereoselective Total Synthesis
of Leiocarpin C and (+)-Goniodiol

J. S. Yadav; V. Hari Krishna; A. Srilatha; R. Somaiah; B. V. Subba Reddy

doi:10.1055/s-0030-1257858

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Synthesis 2010(17): 3004-3012
DOI: 10.1055/s-0030-1257858

PAPER

Stereoselective Total Synthesis of Leiocarpin C and (+)-Goniodiol

J. S. Yadav*, V. Hari Krishna, A. Srilatha, R. Somaiah, B. V. Subba Reddy
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad - 500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;

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Publikationsverlauf

Received 9 April 2010
Publikationsdatum:
30. Juli 2010 (online)

Abstract
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Abstract

Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-Emmons olefination, aryl Grignard reaction, hydroboration, stereoselective alkoxy-directed keto-reduction, stereoselective 1,3-anti-allylation, esterification via ozonolysis, and intramolecular lactonization.

Key words

styryl lactones - dihydroxylation - olefination - hydroboration - 1,3-anti-allylation - ozonolysis

References

1a El-Zayat AAE. Ferringi NR. McCloud TG. McKenzie AT. Byrn SR. Cassady JM. Chang C.-J. McLaughlin JL. Tetrahedron Lett. 1987, 26: 955

Google Scholar
1b Sam TW. Chew SY. Matsjeh S. Gan EK. Razak D. Mohamed AL. Tetrahedron Lett. 1987, 28: 2541

Google Scholar
1c Fang X.-P. Anderson JE. Chang C.-J. Fanwick PE. McLaughlin JL. J. Chem. Soc., Perkin Trans. 1 1990, 1655

Google Scholar
1d Fang X.-P. Anderson JE. Chang C.-J. Fanwick PE. McLaughlin JL. Tetrahedron 1991, 47: 9751

Google Scholar
1e Fang X.-P. Anderson JE. Qiu X.-X. Kozlowski JF. Chang C.-J. McLaughlin JL. Tetrahedron 1993, 49: 1563

Google Scholar
2a Gu Z.-M. Fang X.-P. Zeng L. McLaughlin JL. Tetrahedron Lett. 1994, 35: 5367

Google Scholar
2b Fang X.-P. Anderson JE. Smith DL. Wood KV. McLaughlin JL. J. Nat. Prod. 1992, 55: 1655

Google Scholar
3a Mu Q. Tang WD. Liu RY. Li CM. Lou LG. Sun HD. Planta Med. 2003, 69: 826

Google Scholar
3b Pihie AH. Stanslas J. Din LB. Anticancer Res. 1998, 18: 1739

Google Scholar
4 Mu Q. Tang W. Li C. Lu Y. Sun H. Zheng H. Hoa X. Zheng Q. Wu N. Lou L. Xu B. Heterocycles 1999, 51: 2969

Crossref Google Scholar
5 Mu Q. Li CM. He YN. Sun HD. Zheng HL. Lu Y. Zheng QT. Jiang RW. Chin. Chem. Lett. 1999, 10: 135

Google Scholar
6a Collett LA. Davies-Coleman MT. Rivett DEA. Prog. Chem. Org. Nat. Prod. 1997, 181

Google Scholar
6b Talapatra SK. Basu D. Deb T. Goswami S. Talapatra B. Indian J. Chem., Sect. B 1985, 24: 29

Google Scholar
6c Alkofahi A. Ma WW. Mckenzie AT. Byrn SR. Mclaughlin JL. J. Nat. Prod. 1989, 52: 1371

Google Scholar
6d Tsubuki M. Kanai K. Honda T.
J. Chem. Soc., Chem. Commun. 1992, 1640

Google Scholar
6e Tsubuki M. Kanai K. Nagase H. Honda T. Tetrahedron 1999, 55: 2493

Google Scholar
7a Yadav JS. Rao BM. Rao KS. Reddy BVS. Synlett 2008, 1039

Google Scholar
7b Yadav JS. Reddy PMK. Reddy PV. Tetrahedron Lett. 2007, 46: 1037

Google Scholar
7c Yadav JS. Rao KV. Prasad AR. Tetrahedron Lett. 2006, 47: 3773

Google Scholar
7d Yadav JS. Srinivas R. Sathaiah K. Tetrahedron Lett. 2006, 47: 1603

Google Scholar
7e Yadav JS. Raju AK. Rao PP. Rajaiah G. Tetrahedron: Asymmetry 2005, 16: 3283

Google Scholar
8 Yadav JS. Ramreddy N. Harikrishna V. Reddy BVS. Tetrahedron Lett. 2009, 50: 1318

Crossref Google Scholar
9a Bates EB. Jones ERH. Whiting MC. J. Chem. Soc. 1954, 1854

Google Scholar
9b Eguchi T. Koudate T. Kakinuma K. Tetrahedron 1993, 49: 4527

Google Scholar
10 Trost BM. Chisholm JD. Wrobleski ST. Jung M.
J. Am. Chem. Soc. 2002, 124: 12420

Crossref Google Scholar
11a Yadav JS. Ramreddy N. Harikrishna V. Reddy BVS. Tetrahedron Lett. 2009, 50: 1318

Google Scholar
11b Yadav JS. Chandrasekhar S. Sumitra G. Rajashekar K. Tetrahedron Lett. 1996, 37: 6603

Google Scholar
12a Still WC. Gennari C. Tetrahedron Lett. 1983, 24: 4405

Google Scholar
12b Ando K. J. Org. Chem. 1997, 62: 1934

Google Scholar
12c Sabitha G. Sudhakar K. Yadav JS. Tetrahedron Lett. 2006, 47: 8599

Google Scholar
13 Suemune H. Oda K. Saeki S. Sakai K. Chem. Pharm. Bull. 1988, 36: 172

Google Scholar
14a De Brabander J. Vandewalle M. Synthesis 1994, 855

Google Scholar
14b Watanabe T. Imaizumi T. Chinen T. Nagumo Y. Shibuya M. Usui T. Kanoh N. Iwabuchi Y. Org. Lett. 2010, 12: 1040

Google Scholar
15a Marshall JA. Sedrani R. J. Org. Chem. 1991, 56: 5496

Google Scholar
15b Marshall JA. Garofalo AW. Sedrani RC. Synlett 1992, 643

Google Scholar
15c Marshall JA. Garofalo AW.
J. Org. Chem. 1993, 58: 3675

Google Scholar
16 White JD. Kuntiyong P. Lee TH. Org. Lett. 2006, 8: 6039

Crossref Google Scholar
17 Henry N. Robertson MN. Marquez R. Tetrahedron Lett. 2007, 48: 6088

Crossref Google Scholar
18a Yadav JS. Rami Reddy N. Harikrishna V. Reddy BVS. Tetrahedron Lett. 2009, 50: 1318

Google Scholar
18b Yadav JS. Chander MC. Tetrahedron Lett. 1990, 31: 4349

Google Scholar
18c Jin Y. Liu P. Wang J. Baker R. Huggins J. Chu C. J. Org. Chem. 2003, 68: 9012

Google Scholar
19a Dubost C. Marko IE. Ryckmans T. Org. Lett. 2006, 8: 5137

Google Scholar
19b Rajesh K. Suresh V. Paul selvam JJ. Chantibabu D. Venkateswarlu Y. Helv. Chim. Acta 2010, 93: 147

Google Scholar
20 Gallos JK. Damianous KC. Dellios CC. Tetrahedron Lett. 2001, 42: 5769

Crossref Google Scholar
21 Popsavin V. Benedekovic G. Sreco B. Popsavin M. Francuz J. Kojic V. Bogdanovic G. Org. Lett. 2007, 9: 4235

Crossref Google Scholar
22a Ghosh S. Nageshwerrao C. Dutta S. Synlett 2007, 1464

Google Scholar
22b Takahashi T. Miyazawa M. Tsuji J. Tetrahedron Lett. 1985, 26: 5139

Google Scholar