Formal synthesis of 14-membered unsymmetrical bis-macrolactone, (-)-colletodiol

被引：5

作者：

Khomane, Navnath B. ^{[1
,2
]}

Kumar, Rayala Naveen ^{[1
]}

Mali, Prakash R. ^{[1
,2
]}

Shirsat, Prashishkumar K. ^{[1
,2
]}

Meshram, H. M. ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Med Chem & Biotechnol Div, Hyderabad 500007, Andhra Pradesh, India

[2] Acad Sci & Innovat Res, New Delhi 110025, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 50期

关键词：

Colletodiol; Macrolactonization; Sharpless dihydroxylation; Horner-Wadsworth-Emmons olefination; Pinnik oxidation; 1ST TOTAL-SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; RITTEROSTATIN G(N)1(N); ALDOL REACTION; COLLETODIOL; GRAHAMIMYCIN; BIOACTIVITY; MACROLIDES; EFFICIENT; CONFIGURATION;

D O I：

10.1016/j.tetlet.2017.11.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formal synthesis of 14-membered unsymmetrical bis-macrolactone, (-)-colletodiol was accomplished from homopropargylic alcohol derivative. Building of the two different hydroxy acid fragments from the same intermediate of homoallylic alcohol was particularly advantageous. A Sharpless asymmetric dihydroxylation, homologation of carbon chain, a Pinnick oxidation, and a macrolactonization to assemble the 14-membered macrodiolide were the additional salient features of this convergent synthesis. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：4687 / 4690

页数：4

共 60 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].