Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance

Antonio Rizzo; Dirk Trauner

doi:10.1021/acs.orglett.8b00353

Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance

Antonio Rizzo, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

An approach toward (-)-enterocin, an antibiotic isolated from Streptomyces hygroscopicus, is described. Its compact, heavily oxidized protoadamantane core represents a daunting challenge for an efficient synthesis. Convergent assembly of its 2-oxabicyclo[3.3.1]nonane core with a cuprate-mediated Barbier reaction is disclosed. Its functionalization to a suitable substrate for a biomimetic aldol to close the final ring of the natural product is evaluated.

Original language	English (US)
Pages (from-to)	1841-1844
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.8b00353
State	Published - Apr 6 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00353

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abstract = "An approach toward (-)-enterocin, an antibiotic isolated from Streptomyces hygroscopicus, is described. Its compact, heavily oxidized protoadamantane core represents a daunting challenge for an efficient synthesis. Convergent assembly of its 2-oxabicyclo[3.3.1]nonane core with a cuprate-mediated Barbier reaction is disclosed. Its functionalization to a suitable substrate for a biomimetic aldol to close the final ring of the natural product is evaluated.",

author = "Antonio Rizzo and Dirk Trauner",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Trauner, Dirk

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Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance

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