Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1-C13 fragment of bistramide-A

被引：10

作者：

Yadav, Jhillu Singh ^{[1
]}

Gyanchander, Eppa ^{[1
]}

Mishra, Anand Kumar ^{[1
]}

Adithya, Peddapuram ^{[1
]}

Das, Saibal ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 44期

关键词：

Tetrahydropyrans; Iodine catalyzed allylation; Non Evans aldol; Isomerization; Bistramide A; CHONDROMYCES-SPECIES MYXOBACTERIA; STEREOSELECTIVE TOTAL-SYNTHESIS; LEUCASCANDRA-CAVEOLATA; CYTOSTATIC MACROLIDES; TETRAHYDROPYRAN; CONSTRUCTION; POLYETHER; ACTIN; STEREOISOMER; ELUCIDATION;

D O I：

10.1016/j.tetlet.2013.08.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5879 / 5882

页数：4

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