Chemoenzymatic Synthesis of trans-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene

被引：9
|
作者：
Carlos Ramos, Juan [1 ]
Brovetto, Margarita [1 ]
Seoane, Gustavo A. [1 ]
机构：
[1] Univ Republica, Fac Quim, Dept Quim Organ, Montevideo 1157, Uruguay
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 08期
关键词：
STEREOSELECTIVE-SYNTHESIS; ASIMICIN; DIHYDROXYLATION; INHIBITORS; THF;
D O I：
10.1021/ol400650v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.
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页码：1982 / 1985
页数：4
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