Stereoselective total synthesis of nemorosone

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The highly stereoselective total synthesis of nemorosone via a new approach to the bicyclo[3.3.1]nonane-2,4,9-trione core which features intramolecular cyclopropanation of an α-diazo ketone, stereoselective alkylation at the C8 position, and regioselective ring-opening of cyclopropane is described. The total synthesis of nemorosone includes chemo- and stereoselective hydrogenation directed by the internal alkene.

Original languageEnglish
Pages (from-to)5098-5107
Number of pages10
JournalJournal of Organic Chemistry
Volume77
Issue number11
DOIs
Publication statusPublished - 2012 Jun 1

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Alkylation
Alkenes
Ketones
Hydrogenation
nemorosone
cyclopropane
bicyclo(3.3.1)nonane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective total synthesis of nemorosone. / Uwamori, Masahiro; Saito, Aya; Nakada, Masahisa.

In: Journal of Organic Chemistry, Vol. 77, No. 11, 01.06.2012, p. 5098-5107.

Research output: Contribution to journalArticle

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