Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization

Takayuki Doi, Yusuke Iijima, Masaru Takasaki, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

(Chemical Equation Presented) The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear 7-methylene-2,10- undecadienyl acetate is described. The π-allylpalladium intermediate underwent intramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecular Heck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety and transformation of the vinyl group to an exo-methylene unit provided 3, which is the known synthetic intermediate of dimethyl gloiosiphone A (2).

Original languageEnglish
Pages (from-to)3667-3671
Number of pages5
JournalJournal of Organic Chemistry
Volume72
Issue number10
DOIs
Publication statusPublished - 2007 May 11
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization'. Together they form a unique fingerprint.

Cite this