Formal total synthesis of hemibrevetoxin B by a convergent strategy |
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Authors: | Kenshu Fujiwara Hidetoshi Kawai Takanori Suzuki |
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Institution: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | Concise construction of the trans-fused 7/7/6/6 tetracyclic ether part of hemibrevetoxin B (1) was achieved by a convergent strategy based on coupling reaction of an acyl anion equivalent, reductive cyclization of an α,ε-dihydroxyketone, and introduction of a methyl group at the central ring junction by the Nicolaou method. The resultant tetracyclic ether was transformed into the known intermediate, which was already converted to 1 by the Yamamoto group, thereby completing the formal total synthesis of 1. |
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Keywords: | Polyether Hemibrevetoxin B Natural product synthesis Acyl anion equivalent Convergent synthesis |
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