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Total synthesis of (±)-nakamurol-A and its 13-epimer: tentative assignment of the C-13 relative configuration

✍ Scribed by Josep Bonjoch; Javier Cuesta; Sandra Dı́az; Asensio González

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
156 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general approach to the structure of thelepogan-type diterpenoids has been developed and its application to the ®rst total synthesis of (þ)-nakamurol-A is described. The key steps involve: (i) a diastereoselective dimethylzinc addition to an endocyclic enone followed by enolate trapping; (ii) a Sakurai allylation of an exocyclic enone; and (iii) a Wacker chemoselective oxidation. The 1 H NMR data for the synthetic nakamurol-A and its C-13 epimer allow a tentative assignment of the relative con®guration at C-13 of the natural product.

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