Optically active albolic acid and ceroplastol II, 5–8–5-membered tricyclic sesterterpenoids, were stereoselectively synthesised from two C10 synthons (iridoids)via CrCl2-condensation, lactol-regulated silyloxy–Cope rearrangement with a normally disfavoured boat transition geometry, TiCl2-ring closure, and C5-homologation.
N. Kato, H. Kataoka, S. Ohbuchi, S. Tanaka and H. Takeshita, J. Chem. Soc., Chem. Commun., 1988, 354 DOI: 10.1039/C39880000354
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