A modular total synthesis of aculeatins A, B, E, F and 6-epi-aculeatins E, F

被引：15
|
作者：
Ramana, C. V. [1 ]
Pandey, Sunil Kumar [1 ]
机构：
[1] Natl Chem Lab, Pune 411008, Maharashtra, India
来源：
TETRAHEDRON | 2010年 / 66卷 / 01期
关键词：
Natural products synthesis; Aculeatins; Alkyne-oxirane coupling; Oxidative spiroketalization; Sonogashira coupling; DIVERSITY-ORIENTED SYNTHESIS; CARBOHYDRATE-BASED APPROACH; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE HYDROGENOLYSIS; ABSOLUTE-CONFIGURATIONS; MPM; 4-METHOXYBENZYL; FOCUSED LIBRARY; BENZYL; SONOGASHIRA; DERIVATIVES;
D O I：
10.1016/j.tet.2009.10.058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of aculeatins A, B. E and F confirming the assigned absolute configuration of recently isolated aculeatins E and F is documented. A convergent approach has been designed by the addition of both the terminal units (phenol and side chain) at an advanced stage. The central 1,3,5-triol unit with the requisite stereochemistry was prepared from the commercially available alpha-D-glucoheptonic-gamma-lactone. Selective O-debenzylation during the hydrogenolysis of the diyne intermediate and the one pot phenolic oxidation with concomitant spiroketalization highlight the accomplished total syntheses. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：390 / 399
页数：10
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