137819-50-2Relevant articles and documents
Total Synthesis, Stereochemical Revision, and Biological Reassessment of MandelalideA: Chemical Mimicry of Intrafamily Relationships
Willwacher, Jens,Heggen, Berit,Wirtz, Conny,Thiel, Walter,Fürstner, Alois
supporting information, p. 10416 - 10430 (2015/07/07)
MandelalideA and three congeners had recently been isolated as the supposedly highly cytotoxic principles of an ascidian collected off the South African coastline. Since these compounds are hardly available from the natural source, a concise synthesis rou
Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide
Huang, Yuan,Yang, Licheng,Shao, Panlin,Zhao, Yu
, p. 3275 - 3281 (2013/07/26)
We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90-99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.
Total synthesis of (+)-calyculin A and (-)-calyculin B: Asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit
Smith III, Amos B.,Friestad, Gregory K.,Barbosa, Joseph,Bertounesque, Emmanuel,Hull, Kenneth G.,Iwashima, Makoto,Qiu, Yuping,Salvatore, Brian A.,Spoors, P. Grant,Duan, James J.-W
, p. 10468 - 10477 (2007/10/03)
An asymmetric synthesis of the stereochemically fully endowed C(9-25) spiroketal fragment (+)-BC of the calyculins (1-8) is described. Highlights of the synthesis include: a highly diastereoselective IBr-induced iodocarbonate cyclization to introduce the
