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 (.vphi.,.vphi.-carotene)

Alain Valla 1 Zo Andriamialisoa Benoist Valla Roger Labia Regis Le Guillou Laurent Dufossé 2 Dominique Cartier
1 Chimie et biologie des substances naturelles
2 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments
Abstract : 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 α-, β- 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 Me group from the gem di-Me functionality. [on SciFinder(R)]
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Submitted on : Friday, August 28, 2015 - 3:09:20 PM
Last modification on : Monday, September 2, 2019 - 9:42:15 AM

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Alain Valla, Zo Andriamialisoa, Benoist Valla, Roger Labia, Regis Le Guillou, et al.. 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 (.vphi.,.vphi.-carotene). European Journal of Organic Chemistry, Wiley-VCH Verlag, 2007, 2007 (4), pp.711--715. ⟨10.1002/ejoc.200600794⟩. ⟨hal-01188167⟩

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