70475-68-2Relevant articles and documents
A Simple, Stereocontrolled Synthesis of E,Z-1,5-Dienes
Cadogan, J. I. G.,Buchan, Caroline M.,Gosney, Ian,Hamill, Brendan J.,McLaughlin, Leo M.
, p. 325 - 326 (1982)
The readily available 3,3-dioxide (1) of 3-thiabicycloheptane-6,7-dicarboxylic anhydride acts as a general synthetic precursor for E,Z-1,5-dienes such as (4a-e) via functionalisation followed by thermal extrusion of SO2.
Coibacins a and b: Total synthesis and stereochemical revision
Carneiro, Vania M. T.,Avila, Carolina M.,Balunas, Marcy J.,Gerwick, William H.,Pilli, Ronaldo A.
, p. 630 - 642 (2014/04/03)
The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.
Total synthesis of (+)-13,14-threo-densicomacin
Wang,Tie-Lin, Wang,Hu,Eric, Hu X.,Cassady,Cassady, John M.
, p. 9301 - 9304 (2007/10/02)
The title compound was synthesized from propargyl alcohol and L-glutamic acid via a convergent approach using Sharpless asymmetric epoxidation and asymmetric dihydroxylation for the introduction of chiral centers and Pd0-catalyzed coupling for construction of the carbon skeleton.
