133709-72-5Relevant articles and documents
Biotin biosynthesis: Preparation of the postulated intermediate thiol
Even, L.,Florentin, D.,Marquet, A.
, p. 758 - 768 (2007/10/02)
Previous work in our group led us to postulate thiol 3 as the first intermediate in the biotransformation of dethiobiotin 1 into biotin 2.A new synthesis of this thiol is described here starting from the lactone 4, an intermediate in the Hofmann La Roche industrial synthesis of biotin.After the failure of the Wittig approach, the side-chain was successfully introduced through a Grignard addition to the lactone followed by reduction of the ketone.Deoxygenation of the xanthate afforded the protected alcohol 29.To obtain the deprotected hydroxy acid 34a it was necessary to oxidize the double bond before the debenzylation of the imidazolidinone ring.The acid 34a was readily transformed into 3.Keywords: biotin / biosynthesis / alcohol deoxygenation / debenzylation