Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions:: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine

被引：20

作者：

Pohmakotr, Manat ^{[1
]}

Prateeptongkum, Saisuree ^{[1
]}

Chooprayoon, Soontorn ^{[1
]}

Tuchinda, Patoomratana ^{[1
]}

Reutrakul, Vichai ^{[1
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand

来源：

TETRAHEDRON | 2008年 / 64卷 / 10期

关键词：

cyclization; alpha-sulfinyl carbanion; (+/-)-tashiromine; (+/-)-indolizidine 167B; (+/-)-indolizidine 209D;

D O I：

10.1016/j.tet.2008.01.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-Indolizidines 167B and 209D, their epimers and (+/-)-tashiromine have been successfully synthesized, starting from simple gamma- or alpha-lactams. The strategy involves the cyclization of alpha-sulfinyl carbanion onto the carbonyl group of the lactam ring as the key step, leading to the indolizidines containing the phenylsulfinyl group, which are used as precursors for the preparation of the title compounds. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2339 / 2347

页数：9

共 13 条

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TETRAHEDRON, 2012, 68 (25) : 5025 - 5030
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Yu. N. Bubnov
E. V. Klimkina
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Russian Chemical Bulletin, 1998, 47 : 941 - 949
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JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15): : 4543 - 4552
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ORGANIC LETTERS, 2003, 5 (04) : 583 - 585

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