130127-81-0Relevant articles and documents
Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core
Yang, Sehui,Park, Euijin,Kim, Jimin
, p. 667 - 670 (2021)
Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C6F5)3 was crucial for the stereoselective tr
Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes
Higashino, Masato,Ikeda, Naoko,Shinada, Tetsuro,Sakaguchi, Kazuhiko,Ohfune, Yasufumi
supporting information; experimental part, p. 422 - 425 (2011/03/21)
A novel silyl group-directed anti-SN2′ reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of α-hydroxy-α-alkenylsilanes with a TBS or TIPS group gave the anti-SN2′ product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group.
(+)-Zaragozic acid C: Synthesis and related studies
Carreira, Erick M.,Du Bois
, p. 8106 - 8125 (2007/10/02)
The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)2·H2O]2 for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of γ-alkoxy-α,β-trans enones, and (3) nucleophilic addition of Me3SiC≡CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.