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Total Synthesis of (-)-Enigmazole A.

Abstract
A highly convergent, stereocontrolled total synthesis of the architecturally complex marine sponge metabolite (-)-enigmazole A has been achieved. Highlights include an unprecedented late-stage large-fragment Petasis-Ferrier union/rearrangement, a multicomponent Type I Anion Relay Chemistry (ARC) tactic, and a dithiane-epoxide union in conjunction with an oxazole-directed stereoselective reduction.
AuthorsYanran Ai, Mariya V Kozytska, Yike Zou, Anton S Khartulyari, Amos B Smith 3rd
JournalJournal of the American Chemical Society (J Am Chem Soc) Vol. 137 Issue 49 Pg. 15426-9 (Dec 16 2015) ISSN: 1520-5126 [Electronic] United States
PMID26632969 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)
Chemical References
  • Macrolides
  • Organophosphorus Compounds
  • Oxazoles
  • enigmazole A
Topics
  • Macrolides (chemical synthesis, chemistry)
  • Molecular Structure
  • Organophosphorus Compounds (chemical synthesis, chemistry)
  • Oxazoles (chemical synthesis, chemistry)

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