A short synthesis of (+)-β-lycorane by asymmetric conjugate addition cascade

被引：17

作者：

Nishimura, Katsumi ^{[1
]}

Fukuyama, Naoshi ^{[1
]}

Yasuhara, Tomohisa ^{[1
]}

Yamashita, Mitsuaki ^{[1
]}

Sumiyoshi, Takaaki ^{[1
]}

Yamamoto, Yasutomo ^{[2
]}

Yamada, Ken-ichi ^{[1
]}

Tomioka, Kiyoshi ^{[1
,2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kodo, Kyotanabe 6100395, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 39期

关键词：

Chiral ligand; Asymmetric synthesis; Organolithiums; Conjugate addition; Lycorane; ALPHA; BETA; CHI; PSI-UNSATURATED BISPHOSPHINE OXIDE; ARYLLITHIUM REAGENTS-STRUCTURE; ALDOL TANDEM CYCLIZATION; CHIRAL LIGAND; LITHIUM AMIDE; OMEGA-OXO-ALPHA; BETA-UNSATURATED ESTERS; MICHAEL CYCLIZATION; ORGANIC-SYNTHESIS; L-TYROSINE; ORGANOLITHIUM;

D O I：

10.1016/j.tet.2015.03.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral diether ligand-controlled asymmetric conjugate addition of organolithiums to nona-2,7-dienedioate and subsequent intramolecular conjugate addition of the enolate intermediate gave alltrans trisubstituted cyclohexanes with high ee and yields. Using this methodology, an efficient short asymmetric total synthesis of (+)-beta-lycorane was accomplished in 33% overall yield through five steps from the dienedioate. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7222 / 7226

页数：5

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