期刊
TETRAHEDRON
卷 69, 期 1, 页码 377-386出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.10.012
关键词
Kalafungin; Frenolicin B; Staunton-Weinreb annulation; Pyranonaphthoquinone
资金
- Australian Research Council through the Centres of Excellence program
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.
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