804559-44-2Relevant articles and documents
Synthesis of a proposed biosynthetic intermediate of a marine cyclic ether brevisamide for study on biosynthesis of marine ladder-frame polyethers
Shirai, Tomohiro,Kuranaga, Takefumi,Wright, Jeffrey L.C.,Baden, Daniel G.,Satake, Masayuki,Tachibana, Kazuo
scheme or table, p. 1394 - 1396 (2010/04/25)
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
Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclization strategy
Meilert, Kai,Brimble, Margaret A.
, p. 2184 - 2192 (2008/02/05)
The enantioselective synthesis of the bis-spiroacetal fragment of the shellfish toxins, spirolides B 1 and D 2, is reported. The carbon framework was constructed via a Barbier reaction of dihydropyran 10 with aldehyde 11, followed by two oxidative radical cyclizations to construct the bis-spiroacetal ring system. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor 21. The initial unsaturated bis-spiroacetals 9a-d underwent equilibration during epoxidation to trans-epoxide 24 that was converted to tertiary alcohol 7. The Royal Society of Chemistry 2006.
Synthesis of the bis-spiroacetal moiety of spirolides B and D
Meilert, Kai,Brimble, Margaret A.
, p. 3497 - 3500 (2007/10/03)
(Chemical Equation Presented) An enantioselective synthesis of the bis-spiroacetal fragment of spirolides B and D is reported. The carbon framework was constructed via Barbier reaction of dihydropyran 3 with aldehyde 4, followed by a double oxidative radi
Highly diastereo- and enantioselective reagents for aldehyde crotylation
Hackman, Blaine M.,Lombardi, Pamela J.,Leighton, James L.
, p. 4375 - 4377 (2007/10/03)
(Chemical Equation Presented) Two new, crystalline solid, storable, and highly enantioselective reagents for aldehyde crotylation have been developed. Both (cis and trans) crotylsilane reagents are easily prepared in bulk, require trivial reaction conditi
