CaltechTHESIS
  A Caltech Library Service

A Convergent Synthetic Route to the Tunicamycin Antiobiotics. Synthesis of (+)-Tunicamycin V

Citation

Gin, David Y. (1994) A Convergent Synthetic Route to the Tunicamycin Antiobiotics. Synthesis of (+)-Tunicamycin V. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/p6qx-ng34. https://resolver.caltech.edu/CaltechTHESIS:05072013-095813413

Abstract

A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include: (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product; and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a preformed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly convergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Myers, Andrew G.
Thesis Committee:
  • Unknown, Unknown
Defense Date:10 December 1993
Record Number:CaltechTHESIS:05072013-095813413
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:05072013-095813413
DOI:10.7907/p6qx-ng34
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:7667
Collection:CaltechTHESIS
Deposited By: Benjamin Perez
Deposited On:07 May 2013 17:35
Last Modified:19 Apr 2021 22:38

Thesis Files

[img]
Preview
PDF - Final Version
See Usage Policy.

43MB

Repository Staff Only: item control page