A Synthetic Approach to Several C7-Carbasugars via a Key Intramolecular Morita-Baylis-Hillman Reaction.

A new synthetic strategy for C7-carbasugars is developed via an intramolecular Morita-Baylis-Hillman reaction, in which a substituted dial precursor prepared from d-mannose cyclizes smoothly in the presence of DMAP to afford polyhydroxylated cyclohex-1-enecarbaldehyde with good yield. By employment of the cyclization products as key intermediates, the first syntheses of carbasugar ester 1 and epicorepoxydon A, as well as practical syntheses of epoxydines B and C, (-)-MK7607, (-)-streptol, and (-)-gabosine E are achieved.