Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy

被引：2

作者：

Schrank, Cassandra L. ^{[1
,2
]}

Danneman, Michael W. ^{[1
]}

Prebihalo, Emily A. ^{[1
]}

Anderson, Robert E. ^{[1
]}

Gibson, Tyler J. ^{[1
]}

Wuest, William M. ^{[2
]}

Mullins, Richard J. ^{[1
]}

机构：

[1] Xavier Univ, Dept Chem, 3800 Victory Pkwy, Cincinnati, OH 45207 USA

[2] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 23期

关键词：

Conjugate addition; Allylstannanes; Oxazolidinone; Pilosinine; Stereodivergent; C'D'E'F'-RING-SYSTEM; CHIROSPECIFIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; BIOLOGICAL-ACTIVITY; FORMAL SYNTHESIS; ACID; PILOCARPINE; MODE;

D O I：

10.1016/j.tetlet.2020.151945

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (-)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidinone auxiliary. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：3

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