79563-27-2Relevant articles and documents
Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction
Gerstner, Nels C.,Adams, Christopher S.,Tretbar, Maik,Schomaker, Jennifer M.
, p. 13240 - 13243 (2016)
A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice
Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem
Miyata, Okiko,Shinada, Tetsuro,Ninomiya, Ichiya,Naito, Takeaki
, p. 2421 - 2438 (2007/10/03)
A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to α,β-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem.
Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins
Simpson, Thomas J.,Smith, Robert W.,Westaway, Susan M.,Willis, Christine L.,Buss, Antony D.,Cannell, Richard J. P.,Dawson, Michael J.,Rudd, Brian A. M.
, p. 5367 - 5370 (2007/10/03)
A convergent synthesis of (3R, 5Z, 8E, 10R)-3-hydroxy-8,10-dimethyl-11-phenylundec-5,8-dienoic acid 4, a putative hexaketide intermediate in the biosynthesis of the squalestatins, is described. A key step in the assembly of the carbon framework is the coupling of alkyne 19 with allylic bromide 13 giving, after further functional group manipulations, the target compound as a single diastereomer. The approach may be adapted for the preparation of the corresponding (3S, 5Z, 8E, 10R)-isomer as well as for the incorporation of carbon-13 labels required for biosynthetic studies.