Synthesis of a proposed biosynthetic intermediate of a marine cyclic ether brevisamide for study on biosynthesis of marine ladder-frame polyethers

A proposed biosynthetic intermediate of brevisamide comprising a linear backbone with an E-olefin functionality was synthesized for biosynthetic studies on the marine ladder-frame polyethers. A monocyclic ether alkaloid, brevisamide ( 1) was isolated from the dinoflagellate Karenia brevis that produ...

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Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 10; pp. 1394 - 1396
Main Authors Shirai, Tomohiro, Kuranaga, Takefumi, Wright, Jeffrey L.C., Baden, Daniel G., Satake, Masayuki, Tachibana, Kazuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.03.2010
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GYMNODINIUM
DINOFLAGELLATE KARENIA-BREVIS
CHIRAL SYNTHESIS
PTYCHODISCUS-BREVIS
LASALOCID-A
POLYCYCLIC ETHERS
ORGANOBORANES
CONVERGENT STRATEGIES
BREVETOXINS
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Summary:A proposed biosynthetic intermediate of brevisamide comprising a linear backbone with an E-olefin functionality was synthesized for biosynthetic studies on the marine ladder-frame polyethers. A monocyclic ether alkaloid, brevisamide ( 1) was isolated from the dinoflagellate Karenia brevis that produces a variety of ladder-frame polyethers. Its proposed biosynthetic intermediate ( 2) comprising a linear backbone with an E-olefin functionality was synthesized for biosynthetic studies on the marine ladder-frame polyethers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.01.013