Synthesis and Absolute Configuration of the Antiparasitic Furanosesquiterpenes (-)-Furodysin and (-)-Furodysinin. Camphor as a Six-Membered Ring Chiral Pool Template

Article abstract of DOI:10.1021/jo00001a069

The syntheses of (-)-furodysin ((-2)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites.This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes.This has been found to be a general phenomenon in the camphor system.Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-memberedrings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.