Novel concepts in directed biaryl synthesis - Part 76 - First synthesis ofmastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol

The first synthesis of mastigophorenes A and B by oxidative phenolic coupli ng of partially protected derivatives of their joint natural monomeric half , herbertenediol, is described. The synthesis starts from this diol itself or from the corresponding aldehyde, both available by isolation from the li verwort, Herbertus aduncus. After transformation of herbertenediol to a che mically appropriate monophenolic coupling precursor, the oxidative dehydrod imerization was brought about using (tert-BuO)(2), followed by deprotection to give mastigophorenes A and B in their 'natural' atropisomeric ratio, as isolated from the liverwort. (C) 1998 Elsevier Science Ltd. All rights res erved.