Robert M. Kennedy

A synthesis of 19-dehydroamphoteronolide B

Abstract The four fragments A - D previously prepared for the synthesis of amphoteronolide B have been assembled to provide the titled compound. This assembly represents a formal synthesis of amphoteronolide B.

Stereochemical requirements for fragmentation of homoallylic epoxy alcohols

Abstract The fragmentation of 5,6-epoxynorbornan-2-ol and 5,6-epoxynorbornan-2-one have been studied under both acidic and basic conditions. These processes show a clear preference for syn periplanar alignment of breaking bonds.

A new stereospecific annulation

Abstract A new, high yield, two-step annulation method has been developed which features stereospecific formation of three contiguous asymmetric centers.

Stereocontrol of the metal-ammonia reduction: formation of either cis- or trans-fused decalones from a common intermediate

Abstract Octalone 2 is reduced by lithium-ammonia to the cis-fused decalone, whereas octalone 7 undergoes lithium-ammonia reduction to provide exclusively the trans-fused isomer.