Construction of eight-membered ether rings by olefin geometry-dependent internal alkylation: First asymmetric total syntheses of (+)-3-(E)- and (+)-3-(Z)-pinnatifidenyne

Hyoungsu Kim, Won Jun Choi, Jaeyoon Jung, Sanghee Kim, Deukjoon Kim

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

The first and highly stereoselective asymmetric total syntheses of eight-membered ring ether marine natural products (+)-3-(E)-pinnatifidenyne and (+)-3-(Z)-pinnatifidenyne have been accomplished. Notable features of our syntheses include a novel and efficient construction of oxocene 5 by a highly stereo- and regioselective internal alkylation and direct ketone synthesis of ketone 16 from the α-alkyloxy amide moiety in oxocene 5.

Original languageEnglish
Pages (from-to)10238-10240
Number of pages3
JournalJournal of the American Chemical Society
Volume125
Issue number34
DOIs
StatePublished - 27 Aug 2003

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