Synthetic Studies on Siphonariid Polypropionates: Synthesis and Isomerization of the Caloundrin B Trioxaadamantane Ring System

被引：14

作者：

Beye, Garrison E. ^{[1
]}

Goodman, Jonathan M. ^{[2
]}

Ward, Dale E. ^{[1
]}

机构：

[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada

[2] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

THIOPYRAN ROUTE; ABSOLUTE-CONFIGURATION; MUAMVATIN; MODEL; BACONIPYRONES; METABOLITES; EFFICIENT; FRAGMENTS; ACETALS;

D O I：

10.1021/ol900192q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(1R,3R,5R,7R,8S,9R,10S)-3,5-Diethyl-8,9,10-trimethyl-2,4,6-trioxatricyclo[3.3.1.1(3,7)]decan-1-ol (II), a model of the trioxaadamantane ring system embedded in caloundrin B, was prepared by isomerization of the thermodynamically unstable (9S)-diastereomer (1) in the presence of imidazole. Alternatively, isomerization of I with HF.py or DBU gave the hemiacetal III or its retro-Claisen ester IV, respectively, which represent structural motifs present in the closely related siphonariid polypropionates siphonarin B and baconipyrone C.

引用

页码：1373 / 1376

页数：4

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