Biogenetically Inspired Total Synthesis of Lingzhiol. Design and Synthesis of Axially Chiral N-Heterocyclic Carbene Catalysts.

Author

Krishna Sharmah Gautam, Washington University in St. LouisFollow

Date of Award

Winter 12-15-2016

Author's School

Graduate School of Arts and Sciences

Author's Department

Chemistry

Degree Name

Doctor of Philosophy (PhD)

Degree Type

Dissertation

Abstract

A stereo- and enantio-selective synthesis of lingzhiol has been achieved, mimicking a proposed biogenetic pathway via Brønsted acid-catalyzed semipinacol rearrangement of a 2,3-epoxy alcohol. A new and improved method was developed for alkylation of anilines using a domestic microwave oven. The resulting racemic chiral anilines were resolved via classical resolution and transformed into axially chiral thiazolylidene-based NHC organocatalysts, which were applied to asymmetric benzoin condensation.

Language

English (en)

Chair and Committee

Vladimir B. Birman

Comments

Permanent URL: https://doi.org/10.7936/K79G5K7X

Recommended Citation

Sharmah Gautam, Krishna, "Biogenetically Inspired Total Synthesis of Lingzhiol. Design and Synthesis of Axially Chiral N-Heterocyclic Carbene Catalysts." (2016). Arts & Sciences Electronic Theses and Dissertations. 1006.
https://openscholarship.wustl.edu/art_sci_etds/1006