189265-58-5

Upstream product

• 1027832-85-4 (E)-5-(tert-Butyl-dimethyl-silanyloxy)-pent-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 205692-50-8 (1R,2S,5R)-8-phenylmenthyl (E)-5-hydroxy-2-pentenoate 
• 205692-51-9 ((S)-2-Ethoxy-tetrahydro-pyran-4-yl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 189265-57-4 (E)-5-(2-Bromo-1-ethoxy-ethoxy)-pent-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 189265-59-6 (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 1027944-30-4 (R)-(2,3,4,6,7,12-Hexahydro-indolo[2,3-a]quinolizin-2-yl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 1025907-17-8 (2S,12bR)-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-2-yl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 189265-60-9 (-)-(4S)-4-((1R,3R,4S)-8-phenylmenthyloxycarbonylmethyl)-N-[2-(indol-3-yl)ethyl]piperidin-2-one 

Relevant academic research and scientific papers

Radical cyclisation with high diastereofacial selectivity: Asymmetric synthesis of (+)-12b-epidevinylantirhine

Radical cyclisation of the chiral α,β-unsaturated ester 1, carried out in the presence of MAD, gives six-membered cyclic acetal 2 diastereoselectively, which is transformed into (+)-12b-epidevinylantirhine 7.

Diastereofacial selectivity of radical cyclization using chiral α,β-unsaturated ester and amide: Investigation of a new chiral synthon synthesis

The chiral α,β-unsaturated ester (3a) gave cyclic acetal (4aA) in a highly diastereoselective manner (>98% de) by radical cyclization, which was carried out in the presence of MAD. Furthermore, 4aA was converted into chiral lactone (9), possessing the stereogenic center with three differentiated C-2 units.