The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics

被引：25
作者：
Donner, Christopher D. [1 ,2 ]
机构：
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia
来源：
TETRAHEDRON | 2013年 / 69卷 / 01期
基金：
澳大利亚研究理事会;
关键词：
Kalafungin; Frenolicin B; Staunton-Weinreb annulation; Pyranonaphthoquinone; PICTET-SPENGLER CYCLIZATION; DIELS-ALDER REACTIONS; FRENOLICIN-B; EFFICIENT SYNTHESIS; BIOLOGICAL-ACTIVITY; RACEMIC FRENOLICIN; (+)-KALAFUNGIN; INHIBITORS; QUINONES; ANALOGS;
D O I：
10.1016/j.tet.2012.10.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A divergent, asymmetric method for the synthesis of pyranonaphthoquinones is reported. The synthetic strategy applies a Staunton-Weinreb annulation between substituted ortho-toluates and the (R)-pyran-2-one 7 to construct the key naphthopyranone intermediates. Stereoselective introduction of either a methyl or propyl C5 alkyl substituent by use of Grignard addition/silane-mediated reduction and a sequence of oxidations gave a series of pyranonaphthoquinones including kalafungin 1, 5-epi-9-methoxykalafungin 34 and 5-epi-frenolicin B 24. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码：377 / 386
页数：10
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