1198463-44-3Relevant articles and documents
Stereoselective synthesis of the C13-C28 subunit of (-)-laulimalide utilizing an α-chlorosulfide intermediate
Raghavan, Sadagopan,Samanta, Pradip Kumar
supporting information, p. 1983 - 1987 (2013/09/24)
A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An α-chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively. Georg Thieme Verlag Stuttgart, New York.
Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide
Trost, Barry M.,Amans, Dominique,Seganish, W. Michael,Chung, Cheol K.
supporting information; experimental part, p. 17087 - 17089 (2010/03/23)
(Chemical Equation Presented) Laulimalide is a structurally unique 20-membered marine macrolide displaying microtubule stabilizing activity similar to that of paclitaxel and the epothilones. The use of atom-economical transformations such as a Rh-catalyze