Open AccessTotal Synthesis of (−)-Enigmazole A
Author(s) -
Yanran Ai,
Mariya V. Kozytska,
Yike Zou,
A. Khartulyari,
Amos B. Smith
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b11540
Subject(s) - chemistry , total synthesis , stereochemistry
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.
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