C.-K. Hwang

Total Synthesis of Brevetoxin A: Part 3: Construction of GHIJ and BCDE Ring Systems

Pivotal intermediates in the total synthesis of brevetoxin A are the BCDE and the GHIJ ring systems. Several of the previously developed methodologies such as hydroxy epoxide cyclizations, hydroxy dithioketal cyclizations, and Pd-catalyzed coupling with bis(cyclic ketene acetal phosphates) were employed to achieve these synthetic goals.

Activation of 6-endo over 5-exo epoxide openings. Ring-selective formation of tetrahydropyran systems and stereocontrolled synthesis of the ABC ring framework of brevetoxin B

A new synthetic strategy for the regio- and stereo-specific synthesis of tetrahydropyran systems involving 6-endo epoxide openings and its applicaiton to the construction of the ABC ring system of brevetoxin B are described.

Stereospecific synthesis of 1,1-dialkylglycosides

A new method for the synthesis of 1,1-dialkylglycosides from glycals by sequential electrophilic and nucleophilic alkylations is described.

Synthesis of a fully functionalized CD ring system of taxol

Key building blocks 16 and 17 related to taxol CD ring system have been synthesized in racemic form via a stereocontrolled and efficient sequence featuring a novel Diels–Alder reaction and oxetane formation.