Journal of Organic Chemistry p. 378 - 387 (1991)
Update date:2022-08-05
Topics:
Vaillancourt, Valerie
Agharahimi, Mohamad R.
Sundram, Uma N.
Richou, Olivier
Faulkner, D. John
Albizati, Kim F.
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.
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