Issue 1, 1989

Synthetic photochemistry. Part 44. Total synthesis of ceroplastol II and albolic acid, 5-8-5-membered tricyclic sesterterpenoid insect wax constituents, via stereocontrolled silyloxy-Cope rearrangement with a normally disfavoured transition state

Abstract

To a 1,5-diene, prepared by CrCl2-mediated condensation of two iridoid synthons, was appended a lactol moiety, which was subjected to a stereocontrolled silyloxy-Cope rearrangement to give, via a normally disfavoured boat transition geometry, a thermolysate, from which the total synthesis of optically active Ceroplastol II and albolic acid, 5-8-5-membered tricyclic sesterterpenoids, was accomplished for the first time.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 165-174

Synthetic photochemistry. Part 44. Total synthesis of ceroplastol II and albolic acid, 5-8-5-membered tricyclic sesterterpenoid insect wax constituents, via stereocontrolled silyloxy-Cope rearrangement with a normally disfavoured transition state

N. Kato, H. Takeshita, H. Kataoka, S. Ohbuchi and S. Tanaka, J. Chem. Soc., Perkin Trans. 1, 1989, 165 DOI: 10.1039/P19890000165

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