Synthesis of (+)-Lentiginosine and Its Pyrrolizidine Analogue Based on Intramolecular Cyclization of α-Sulfinyl Carbanions

被引：19

作者：

Du-a-man, Sakkarin ^{[1
,2
]}

Soorukram, Darunee ^{[1
,2
]}

Kuhakarn, Chutima ^{[1
,2
]}

Tuchinda, Patoomratana ^{[1
,2
]}

Reutrakul, Vichai ^{[1
,2
]}

Pohmakotr, Manat ^{[1
,2
]}

机构：

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

[2] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem, Bangkok 10400, Thailand

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 08期

关键词：

Natural products; Chiral pool; Diastereoselectivity; Carbanions; Cyclization; ASYMMETRIC SYNTHESES; CONCISE SYNTHESES; POLYHYDROXYLATED ALKALOIDS; STEREOSELECTIVE-SYNTHESIS; INDOLIZIDINE ALKALOIDS; MANNOSIDASE INHIBITOR; SYNCYTIUM FORMATION; NATURAL OCCURRENCE; FORMAL SYNTHESIS; D-SWAINSONINE;

D O I：

10.1002/ejoc.201301671

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of (+)-lentiginosine and its pyrrolizidine analogue was accomplished in six steps, starting from L-(+)-tartaric acid. The key step of these syntheses involves the intramolecular cyclization of -sulfinyl carbanions for the construction of the indolizidine or pyrrolizidine ring.

引用

页码：1708 / 1715

页数：8

共 10 条

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