A new biomimetic-like aromatization of the cyclic end groups of terpenoids with stereospecific migration of one of the methyl groups: A convenient route to isorenieratene (phi,phi-carotene)

摘要

The synthesis of isorenieratene, a natural carotenoid isolated from the marine sponge Reniera japonica and from some anoxygenic phototrophic bacteria or nonphotosynthetic actinomycetes, was performed from alpha-, beta- and retro-ionones. In this series of cyclohexenes, this synthesis is the first to include a one-pot aromatization of the cyclic end group with concomitant regioselective migration of one methyl group from the gem dimethyl functionality. (C) Wiley-VCH Verlag GmbH & Co.