Total Synthesis of (−)-Enigmazole A

Total Synthesis of (−)-Enigmazole A

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) tac...

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Veröffentlicht in:Journal of the American Chemical Society 2015-12, Vol.137 (49), p.15426-15429
Hauptverfasser: Ai, Yanran, Kozytska, Mariya V, Zou, Yike, Khartulyari, Anton S, Smith, Amos B
Format: Artikel
Sprache:eng
Schlagworte:
Communication
Macrolides - chemical synthesis
Macrolides - chemistry
metabolites
Molecular Structure
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Oxazoles - chemical synthesis
Oxazoles - chemistry
Porifera
stereochemistry
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Beschreibung
Zusammenfassung: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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b11540