Total synthesis of two γ-butyrolactone containing compounds (Z,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (Z)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide

被引：4

作者：

Nomula, Rajesh ^{[1
]}

Raju, Galla ^{[1
]}

Krishna, Palakodety Radha ^{[1
]}

机构：

[1] CSIR, Indian Inst Chem Technol, Organ & Biomol Chem Div, D211,Discovery Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 43期

关键词：

gamma-Butyrolactones; Jacobsen's kinetic resolution; Regioselective epoxide ring-opening; Lindlar's catalyst; Total synthesis; KINETIC RESOLUTION; TERMINAL EPOXIDES; FACILE SYNTHESIS; ANALOGS;

D O I：

10.1016/j.tetlet.2014.09.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (2,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (2)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide was accomplished using Jacobsen hydrolytic kinetic resolution, Ohira-Bestmann reaction, regioselective allcyne addition to terminal carbon atom of epoxide, intramolecular TEMPO/BAIB mediated oxidative lactonization and partial hydrogenation as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5976 / 5978

页数：3

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