Application of the hydroxy-directed Diels-Alder reaction toward the total synthesis of havellockate

Abstract

This thesis describes our efforts into the synthesis of a natural product named havellockate, which was isolated from a soft coral in the Indian Ocean. This highly compact diterpenoid contains a cis- fused hydrindane core that bears eight stereogenic centers as well as a seco- and spiro-lactone. The early part of this thesis details the application of the hydroxy-directed Diels-Alder reaction to provide rapid entry into the core of the molecule. The subsequent chapters describe the four approaches that were investigated for installing the side-chain of this natural product which contains a challenging stereogenic center. These approaches which include two different Claisen rearrangements, a Diels-Alder reaction as well as a cuprate addition onto an alpha,beta-unsaturated carbonyl compound are presented in detail.