Extending pummerer reaction chemistry: Application to the assembly of the pentacyclic core of dibromopalau'amine

Ken S. Feldman; Ahmed Yimam Nuriye

doi:10.1021/ol1018322

Extending pummerer reaction chemistry: Application to the assembly of the pentacyclic core of dibromopalau'amine

Ken S. Feldman, Ahmed Yimam Nuriye

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23 Scopus citations

Abstract

A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core.

Original language	English (US)
Pages (from-to)	4532-4535
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	20
DOIs	https://doi.org/10.1021/ol1018322
State	Published - Oct 15 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol1018322

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abstract = "A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core.",

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AB - A pentacyclic model system featuring the trans azabicyclo[3.3.0]octane unit of dibromopalau'amine was prepared with complete diastereoselectivity in the polycyclic core from a tricyclic precursor. The key transformations of this sequence include (a) a Pummerer reaction-mediated oxidative bicyclization, and (b) a Wolff rearrangement-based ring contraction to deliver the strained azabicyclo[3.3.0]octane core.

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Extending pummerer reaction chemistry: Application to the assembly of the pentacyclic core of dibromopalau'amine

Abstract

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