Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation

Masahito Abe, Aya Saito, Masahisa Nakada

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cyclopropanes, and ring-opening reaction of the alkylated cyclopropanes. As a result, α-diazomethyl ketone 10c was found to be the most suitable. The enantioselective intramolecular cyclopropanation to construct the bicyclo[3.3.1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described.

Original languageEnglish
Pages (from-to)1298-1302
Number of pages5
JournalTetrahedron Letters
Volume51
Issue number9
DOIs
Publication statusPublished - 2010 Mar 3

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation'. Together they form a unique fingerprint.

  • Cite this