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

Ken S. Feldman, Ahmed Nuriye

Research output: Contribution to journalArticle

20 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4532-4535
Number of pages4
JournalOrganic Letters
Volume12
Issue number20
DOIs
StatePublished - Oct 15 2010

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octanes
Amines
amines
assembly
chemistry
contraction
rings
azabicyclo(3.3.0)-octane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Extending pummerer reaction chemistry : Application to the assembly of the pentacyclic core of dibromopalau'amine. / Feldman, Ken S.; Nuriye, Ahmed.

In: Organic Letters, Vol. 12, No. 20, 15.10.2010, p. 4532-4535.

Research output: Contribution to journalArticle

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