PMID: 11929254Apr 4, 2002Paper

Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs. A new entry to (-)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (-)-tetracyclic polyprenoid of sedimentary origin

Journal of the American Chemical Society
Kazuaki IshiharaHisashi Yamamoto

Abstract

An enantio- and diastereoselective stepwise cyclization of polyprenoids induced by Lewis acid-assisted chiral Brønsted acids (chiral LBAs) and achiral LBAs is described. In particular, the absolute stereocontrol in the initial cyclization of polyprenoids to form an A-ring induced by chiral LBAs and the importance of the nucleophilicity of the internal terminator in polyprenoids for the relative stereocontrol in subsequent cyclization are demonstrated. (-)-Ambrox was synthesized via the enantioselective cyclization of (E,E)-homofarnesyl triethylsilyl ether with tin(IV) chloride-coordinated (R)-2-(o-fluorobenzyloxy)-2'-hydroxy-1,1'-binaphthyl ((R)-BINOL-o-FBn) and subsequent diastereoselective cyclization with CF(3)CO(2)H.SnCl(4) as key steps. Protection of (E,E)-homofarnesol by a triethylsilyl group increased the enantioselectivity of chiral LBA-induced cyclization and both the chemical yield and diastereoselectivity in the subsequent cyclization. The enantioselective cyclization of homo(polyprenyl)arenes possessing an aryl group was also induced by (R)-BINOL-o-FBn.SnCl(4). Several optically active podocarpa-8,11,13-triene diterpenoids and (-)-tetracyclic polyprenoid of sedimentary origin were synthesized (75-80% ee) by the enan...Continue Reading

Citations

Nov 19, 2013·Tetrahedron·Hisashi Yamamoto
Dec 22, 2007·Journal of the American Chemical Society·Jeremiah A Feducia, Michel R Gagné
Mar 14, 2008·Chemical Communications : Chem Comm·Yu-Jun Zhao, Teck-Peng Loh
Apr 5, 2008·Chemical Communications : Chem Comm·Jun-Feng ZhaoTeck-Peng Loh
Aug 24, 2010·Chemical Communications : Chem Comm·Cheol Hong CheonHisashi Yamamoto
Nov 8, 2007·Bioscience, Biotechnology, and Biochemistry·Arata YajimaGoro Yabuta
Apr 21, 2017·Angewandte Chemie·Heping DengBo Liu
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Mar 17, 2005·Angewandte Chemie·Hisashi Yamamoto, Kentaro Futatsugi
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