862994-98-7Relevant academic research and scientific papers
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
