Consecutive sigmatropic rearrangements in the enantioselective total synthesis of (-)-joubertinamine and (-)-mesembrine

被引：36

作者：

Ilardi, Elizabeth A. ^{[1
]}

Isaacman, Michael J. ^{[1
]}

Qin, Ying-chuan ^{[1
]}

Shelly, Sommer A. ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 16期

基金：

美国国家科学基金会;

关键词：

Sigmatropic rearrangements; Sceletium alkaloids; Mesembrine; Joubertinamine; QUATERNARY CARBON CENTER; ASYMMETRIC-SYNTHESIS; CLAISEN REARRANGEMENT; PINNATOXINS; (+/-)-MESEMBRINE; JOUBERTINAMINE; (+)-MESEMBRINE; CYCLOADDITION; SUBSTITUTION; ALKALOIDS;

D O I：

10.1016/j.tet.2008.10.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Joubertinamine and mesembrine are two related alkaloids isolated from Sceletium plants. From the perspective of chemical synthesis, the major challenge posed by joubertinamine and mesembrine is Undoubtedly the construction of the benzylic quaternary stereogenic center. We became intrigued by the prospect of applying Successive sigmatropic rearrangements to build the key structural features of these alkaloids in enantioselective manner. In this article, We detail Our results in this area, which include the enantioselective total synthesis Of (-)-joubertinamine and (-)-mesembrine. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3261 / 3269

页数：9

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