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A new synthesis of the 2,2,3,5,6,6-substituted tetrahydropyran aplysiapyranoid A and its 5-epimer

✍ Scribed by Jens Hartung; Marco Greb

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
178 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The vanadium(V)-catalyzed oxidation of bromide in the presence of methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate furnished 5,6-trans-5-bromo-6-phenyl-2,2,6-trimethyl-3-methyloxycarbonyltetrahydropyran, which was converted into the marine natural product aplysiapyranoid A and its 5-epimer, via a short sequence of decarboxylative bromination and transition metal-based procedures for transforming a phenyl into a chlorovinyl substituent.

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