Total Synthesis of Ustiloxin D

A. L. Brown, N. L. Fifer, L. Hunter, Quentin I. Churches, P. W.H. Chan, S. B. Cohen, C. A. Hutton

Research output: Chapter in Book/Report/Conference proceedingChapter (Book)Researchpeer-review

Abstract

This account describes the total synthesis of ustiloxin D. A first-generation, chiral pool approach to the functionalized isoleucine precursor was unsuccessful but yielded several interesting observations. A revised strategy was devised in which the concise, high-yielding total synthesis was facilitated by two key processes: an asymmetric allylic alkylation to construct the alkyl–aryl ether and an ammonia–Ugi reaction to construct the isoleucine-containing tripeptide fragment.

Original languageEnglish
Title of host publicationStrategies and Tactics in Organic Synthesis
EditorsMichael Harmata
Place of PublicationLondon UK
PublisherElsevier
Chapter6
Pages169-191
Number of pages23
Volume12
Edition1
ISBN (Print)9780081007563
DOIs
Publication statusPublished - 2016

Publication series

NameStrategies and Tactics in Organic Synthesis
PublisherElsevier
Number1
Volume12
ISSN (Print)18746004

Keywords

  • Asymmetric allylic alkylation
  • Peptide natural products
  • Total synthesis
  • Ugi reaction
  • Ustiloxin

Cite this

Brown, A. L., Fifer, N. L., Hunter, L., Churches, Q. I., Chan, P. W. H., Cohen, S. B., & Hutton, C. A. (2016). Total Synthesis of Ustiloxin D. In M. Harmata (Ed.), Strategies and Tactics in Organic Synthesis (1 ed., Vol. 12, pp. 169-191). (Strategies and Tactics in Organic Synthesis; Vol. 12, No. 1). Elsevier. https://doi.org/10.1016/B978-0-08-100756-3.00006-6