Event Information
Guoqiang Zhou
(Duke University)
METHODS FOR DIRECT CARBON–CARBON BOND FORMATION AND THEIR APPLICATION TO NATURAL PRODUCT SYNTHESIS
Student Exams Seminar
METHODS FOR DIRECT CARBON–CARBON BOND FORMATION AND THEIR APPLICATION TO NATURAL PRODUCT SYNTHESIS
- Abstract:
- Direct carbon–carbon 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-grade solvent open to the air. Using this direct approach as a basis, we have developed methods for the synthesis of -hydroxy thioesters, -keto thioesters, and 1,3-diketones, 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-diketone compounds, 3) a direct crossed-Claisen reaction, and 4) an anti-selective four-component 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-amino cyclic carbamate (ACC) hydrazones, a new technology recently developed in our group.
Ph.D. Dissertation Defense Seminar
Student Exams Seminar