The C3-C21 segment of aflastatin A has been synthesized by converging three segments including the C3-C8 segment, the C9-C15 segment, and the C16-C21 segment. Each segment has been synthesized from a vinylketene silyl N,O-acetal possessing a chiral auxiliary by a wide-range stereocontrol strategy. The C3-C8 segment was constructed in seven steps including the stereoselective vinylogous Mukaiyama alkylation, while the C9-C15 segment and the C16-C21 segment were synthesized using the vinylogous Mukaiyama aldol reaction in seven and eight steps, respectively.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry