Total syntheses and absolute stereochemistry of decarestrictines C1 and C2

被引：31
|
作者：
Mohapatra, Debendra K. [1 ,2 ]
Sahoo, Gokarneswar [1 ]
Ramesh, Dhondi K. [1 ]
Rao, J. Srinivasa [3 ]
Sastry, G. Narahari [3 ]
机构：
[1] Natl Chem Lab CSIR, Div Organ Chem, Pune 411008, Maharashtra, India
[2] Indian Inst Chem Technol CSIR, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
[3] Indian Inst Chem Technol CSIR, Mol Modeling Grp, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 40期
关键词：
Decarestrictines; Sharpless asymmetric epoxidation; Pinnick oxidation; Yamaguchi coupling reaction; Ring-closing metathesis; 1ST TOTAL-SYNTHESIS; SECONDARY METABOLITES; CHOLESTEROL-BIOSYNTHESIS; OLEFIN METATHESIS; INHIBITORS; EFFICIENT; PENICILLIUM; OXIDATION; FAMILY; STRAIN;
D O I：
10.1016/j.tetlet.2009.07.099
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total syntheses of decarestrictines C-1 and C-2 have been described. The synthetic strategy involves a practical and flexible approach using esterification and ring-closing metathesis to unite the acid and alcohol fragments. The acid fragments are enantiomers of each other and have been prepared from L-(-)-malic acid via similar transformations; in Sharpless asymmetric epoxidation, (+)-DET has been used for decarestrictine C-1 and (-)-DET for decarestrictine C-2. The alcohol fragment is identical for both decarestrictines C-1 and C-2 and has been accessed from D-(+)-mannitol. Comparison of the H-1 and C-13 NMR data combined with the computational studies predicts the presence of two conformations without and with hydrogen bonding (conformational isomers I and II for decarestrictine C-1), respectively. The H-1 and C-13 NMR data for decarestrictine C-2 completely agreed with the analytical data reported by Kibayashi et al. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5636 / 5639
页数：4
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