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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
A Synthetic Approach to Several C7-Carbasugars via a Key Intramolecular Morita-Baylis-Hillman Reaction
Yuanliang Jia1, Maolin Wang1, Folei Wu1
1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Abstract:
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.
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