70475-68-2Relevant academic research and scientific papers
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.
Regio- and diastereoselective reductive coupling of vinylepoxides catalyzed by titanocene chloride
Barrero, Alejandro F.,Del Moral, Jose F. Quilez,Sanchez, Elena M.,Arteaga, Jesus F.
, p. 669 - 672 (2006)
The Ti(III)-catalyzed reaction of a series of vinylepoxides leads, with regio- and E-diastereoselectivity control, to good-to-excellent yields of the corresponding homocoupling products. This homocoupling reaction, which involves a new C-C bond-forming method, takes place via a SN2′ process between an allyltitanium species and the starting vinylepoxide. The process can be used for the rapid and efficient formation of highly valuable intermediates for organic synthesis, as well as new interesting homologues of natural products.
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.
Regio- and stereospecific formation of protected allylic alcohols via zirconium-mediated SN2′ substitution of allylic chlorides
Fox, Richard J.,Lalic, Gojko,Bergman, Robert G.
, p. 14144 - 14145 (2008/09/18)
A new, highly regio- and stereospecific SN2′ substitution reaction between a zirconium oxo complex and allylic chloride has been achieved. The resulting allylic alcohol or TBS-protected allylic ether products were isolated in good to excellent yields with a wide range of E-allylic chlorides. A mechanism for the SN2′ allylic substitution consistent with kinetic, stereochemical, and secondary isotope effect studies was proposed. Copyright
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.
