Total synthesis of marine diterpenoid stolonidiol

Marine dolabellane diterpenoid stolonidiol was synthesized from l-ascorbic acid. The method for this total synthesis involves formation of the bicyclo[2.2.1]heptane derivative using a diastereoselective sequential Michael reaction, formation of cyclopentane derivative by the retro-aldol reaction and...

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Bibliographic Details
Published in:Tetrahedron letters 2001-12, Vol.42 (52), p.9233-9236
Main Authors: Miyaoka, Hiroaki, Baba, Tomohiro, Mitome, Hidemichi, Yamada, Yasuji
Format: Article
Language:English
Subjects:
antitumor compounds
marine metabolites
terpenes and terpenoids
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Summary:Marine dolabellane diterpenoid stolonidiol was synthesized from l-ascorbic acid. The method for this total synthesis involves formation of the bicyclo[2.2.1]heptane derivative using a diastereoselective sequential Michael reaction, formation of cyclopentane derivative by the retro-aldol reaction and construction of an 11-membered carbocyclic ring through the intramolecular Horner–Wadsworth–Emmons reaction. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)02032-9