Synthesis studies on the lomaiviticin A aglycone core: Development of a divergent, two-directional strategy

Ken S. Feldman; Brandon R. Selfridge

doi:10.1021/jo4005074

Synthesis studies on the lomaiviticin A aglycone core: Development of a divergent, two-directional strategy

Ken S. Feldman, Brandon R. Selfridge

Chemistry

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15 Scopus citations

Abstract

The enantiomer of the bicyclic lomaiviticin aglycone A core was prepared via a two-directional, divergent approach featuring (1) a double Ireland Claisen rearrangement to establish key core bonds with correct relative stereochemistry and (2) a double olefin metathesis reaction to deliver both cyclohexene rings of the target.

Original language	English (US)
Pages (from-to)	4499-4511
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	78
Issue number	9
DOIs	https://doi.org/10.1021/jo4005074
State	Published - May 3 2013

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo4005074

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title = "Synthesis studies on the lomaiviticin A aglycone core: Development of a divergent, two-directional strategy",

abstract = "The enantiomer of the bicyclic lomaiviticin aglycone A core was prepared via a two-directional, divergent approach featuring (1) a double Ireland Claisen rearrangement to establish key core bonds with correct relative stereochemistry and (2) a double olefin metathesis reaction to deliver both cyclohexene rings of the target.",

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AB - The enantiomer of the bicyclic lomaiviticin aglycone A core was prepared via a two-directional, divergent approach featuring (1) a double Ireland Claisen rearrangement to establish key core bonds with correct relative stereochemistry and (2) a double olefin metathesis reaction to deliver both cyclohexene rings of the target.

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Synthesis studies on the lomaiviticin A aglycone core: Development of a divergent, two-directional strategy

Abstract

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