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). London UK: Elsevier. https://doi.org/10.1016/B978-0-08-100756-3.00006-6
Brown, A. L. ; Fifer, N. L. ; Hunter, L. ; Churches, Quentin I. ; Chan, P. W.H. ; Cohen, S. B. ; Hutton, C. A. / Total Synthesis of Ustiloxin D. Strategies and Tactics in Organic Synthesis. editor / Michael Harmata. Vol. 12 1. ed. London UK : Elsevier, 2016. pp. 169-191 (Strategies and Tactics in Organic Synthesis; 1).
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Brown, AL, Fifer, NL, Hunter, L, Churches, QI, Chan, PWH, Cohen, SB & Hutton, CA 2016, Total Synthesis of Ustiloxin D. in M Harmata (ed.), Strategies and Tactics in Organic Synthesis. 1 edn, vol. 12, Strategies and Tactics in Organic Synthesis, no. 1, vol. 12, Elsevier, London UK, pp. 169-191. https://doi.org/10.1016/B978-0-08-100756-3.00006-6

Total Synthesis of Ustiloxin D. / Brown, A. L.; Fifer, N. L.; Hunter, L.; Churches, Quentin I.; Chan, P. W.H.; Cohen, S. B.; Hutton, C. A.

Strategies and Tactics in Organic Synthesis. ed. / Michael Harmata. Vol. 12 1. ed. London UK : Elsevier, 2016. p. 169-191 (Strategies and Tactics in Organic Synthesis; Vol. 12, No. 1).

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

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Brown AL, Fifer NL, Hunter L, Churches QI, Chan PWH, Cohen SB et al. Total Synthesis of Ustiloxin D. In Harmata M, editor, Strategies and Tactics in Organic Synthesis. 1 ed. Vol. 12. London UK: Elsevier. 2016. p. 169-191. (Strategies and Tactics in Organic Synthesis; 1). https://doi.org/10.1016/B978-0-08-100756-3.00006-6