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Synthesis of the C-ring fragment of cobyric acid

โœ Scribed by Johann Mulzer; Doris Riether


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
127 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


An efficient stereocontrolled synthesis of the C-ring fragment of cobyric acid 1 is described. The key step is an auxiliary controlled conjugate addition of vinyl cuprate to (5S)-menthyloxy-2[5H]-furanone 3.


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A stereoselective synthesis of the EFGH ring fragment of ciguatoxin CTX3C has been achieved through: (i) selective cleavage of a dioxepane acetal C O bond; (ii) radical cyclization to form the oxepane G ring; and (iii) chemoselective ring-closing metathesis of a triene yielding the hexahydrooxonin F