Methods for Direct Carbon-Carbon Bond Formation and Their Application to Natural Product Synthesis

Loading...
Thumbnail Image

Date

2009

Journal Title

Journal ISSN

Volume Title

Repository Usage Stats

402
views
935
downloads

Abstract

Direct carbon&mdashcarbon bond formation via soft enolization and in situ enolate formation provides a straightforward approach to certain key transformations of synthetic organic chemistry. Reactions are generally operationally simple and proceed under mild conditions using untreated, reagent&ndashgrade solvent open to the air. Using this direct approach as a basis, we have developed methods for the synthesis of β&ndashhydroxy thioesters, β&ndashketo thioesters, and 1,3&ndashdiketones, which are key intermediates for the synthesis of natural products, pharmaceuticals, and other biologically relevant compounds. In particular, we describe: 1) a direct aldol addition of simple thioesters, 2) a direct synthesis of 1,3&ndashdiketone compounds, 3) a direct crossed&ndashClaisen reaction, and 4) an anti&ndashselective four&ndashcomponent direct aldol cascade reaction.

Progress toward the total synthesis of apratoxin D is described. The key steps of the synthesis involve the asymmetric alkylation via chiral N&ndashamino cyclic carbamate (ACC) hydrazones, a new technology recently developed in our group.

Department

Description

Provenance

Citation

Citation

Zhou, Guoqiang (2009). Methods for Direct Carbon-Carbon Bond Formation and Their Application to Natural Product Synthesis. Dissertation, Duke University. Retrieved from https://hdl.handle.net/10161/1170.

Collections


Dukes student scholarship is made available to the public using a Creative Commons Attribution / Non-commercial / No derivative (CC-BY-NC-ND) license.