Extending pummerer reaction chemistry: Studies in the palau'amine synthesis area

Ken S. Feldman, Ahmed Yimam Nuriye, Jianfeng Li

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Exploratory oxidative cyclization studies on cyclopentanelated and cyclohexenelated oroidin derivatives utilized Pummerer chemistry to generate pentacyclic structures related to the palau'amine family of sponge metabolites. Stereochemical issues were paramount, and appropriate choice of annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity for all of the core bonds.

Original languageEnglish (US)
Pages (from-to)5042-5060
Number of pages19
JournalJournal of Organic Chemistry
Volume76
Issue number12
DOIs
StatePublished - Jun 17 2011

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Cyclization
Metabolites
Derivatives
oroidin
palau'amine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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Extending pummerer reaction chemistry : Studies in the palau'amine synthesis area. / Feldman, Ken S.; Nuriye, Ahmed Yimam; Li, Jianfeng.

In: Journal of Organic Chemistry, Vol. 76, No. 12, 17.06.2011, p. 5042-5060.

Research output: Contribution to journalArticle

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