Stereoselective synthesis of (+)-decarestrictine L using tandem isomerization followed by C-O and C-C bond formation reaction

被引：5
|
作者：
Banoth, Shivalal [1 ,2 ]
Kanikarapu, Suresh [1 ]
Yadav, Jhillu S. [1 ,2 ]
Mohapatra, Debendra K. [1 ,2 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
[2] Acad Sci & Innovat Res, New Delhi 110001, India
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 39期
关键词：
Natural products; Tandem reaction; trans-2,6-Disubstituted dihydropyran; Mitsunobu inversion; Wacker's oxidation; ENANTIOSELECTIVE SYNTHESIS; CHOLESTEROL-BIOSYNTHESIS; SECONDARY METABOLITES; BICYCLIC CORE; FAMILY; DECARESTRICTINES; IODOCYCLIZATION; PENICILLIUM; INHIBITORS; CONCISE;
D O I：
10.1016/j.tetlet.2016.08.055
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereoselective synthesis of the (+)-decarestrictine L has been described following our own developed iodine-catalyzed tandem isomerization followed by C-O and C-C bond formation reaction for the construction of trans-2,6-disubstituted dihydropyran as the key step. Other important reactions used for this synthesis are 5-exo-trig-iodolactonization, Mitsunobu inversion, and Wacker's oxidation. The total synthesis of the target molecule was achieved in 10 linear steps with 28% overall yield. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4368 / 4370
页数：3
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