477953-48-3Relevant articles and documents
Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling
White, James D.,Quaranta, Laura,Wang, Guoqiang
, p. 1717 - 1728 (2007/10/03)
Two principal subunits of the marine algal toxin (-)-gymnodimine were synthesized. A trisubstituted tetrahydrofuran representing C10-C18 of the toxin was prepared via a highly stereoselective iodine-mediated cyclization of an acyclic alkene bearing a bis-
Silicon tether-aided coupling metathesis: Application to the synthesis of attenol A
Van De Weghe, Pierre,Aoun, Darina,Boiteau, Jean-Guy,Eustache, Jacques
, p. 4105 - 4108 (2007/10/03)
(matrixpresented) A new synthesis of attenol A is described. Key features of this work include a crucial silicon tether-aided coupling metathesis step and the use of iodoetherification as an efficient protection method for 1,5-ene-ols.
Total Synthesis of Tautomycin
Oikawa, Masato,Ueno, Tohru,Oikawa, Hideaki,Ichihara, Akitami
, p. 5048 - 5068 (2007/10/02)
A convergent stereocontrolled synthesis of the antifungal antibiotic tautomycin, a potent protein phosphatases inhibitor, has been achieved first via key aldol coupling of two large subunits, a right-hand C1-C21 ketone and a left-hand aldehyde (left from C22).The C1-C10 segment was synthesized through a remote stereochemical control process using a spiroketal template.After joining with the C11-C18 segment, the spiroketal moiety was selectively constructed.Then the right-hand C1-C21 ketone was synthesized via Roush asymmetric crotylboration.The left-hand aldehyde was prepared from a C21-C26 segment and a dialkylmaleic anhydride segment.Completely stereoselective assemblage of the two subunits, the right-hand and the left-hand, was achieved by employing the Mukaiyama aldol reaction.Further functional group manipulation including desilylation, oxidation at C2, and deprotection of tert-butyl ester with concomitant anhydride formation provided tautomycin which was identical with the natural product.As a preliminary study, derivatizations and degradation of the natural product were also examined to support the total synthesis.