A Convergent Coupling Strategy for the Formation of Polycyclic Ethers:  Stereoselective Synthesis of the BCDE Fragment of Brevetoxin A

Autor: Crimmins, M. T., McDougall, P. J., Emmitte, K. A.
Zdroj: Organic Letters; September 2005, Vol. 7 Issue: 18 p4033-4036, 4p
Abstrakt: A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner−Wadsworth−Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment.
Databáze: Supplemental Index