A NOVEL AND EFFICIENT ROUTE TO CHIRAL A-RING AROMATIC TRICHOTHECANES - THE FIRST ENANTIOCONTROLLED TOTAL SYNTHESIS OF (-)-DEBROMOFILIFORMIN AND (-)-FILIFORMIN

摘要

The first examples of asymmetric dihydroxylation (AD) of the cyclopropylidene derivatives 12a-e followed by enantiospecific 1,2-rearrangement of the resulted diols 13a similar to e to give the optically active cyclobutanones 15a similar to d and 11, and also the first enantiocontrolled total synthesis of (-)-debromofiliformin (7a) and (-)-filiformin (7b) starting from 11 via the regiocontrolled cyclization of the phenolic allyl alcohol 25 to the A-ring aromatic trichothecane 26, were reported. [References: 48]