A short and efficient synthesis of (R)-(−)-sporochnol A

A short and efficient synthesis of (R)-(−)-sporochnol A in five steps and 9% overall yield has been developed. The sequence uses as starting material the easily available enantiopure monoketal derived from 1,4-cyclohexanedione and (R,R)-hydrobenzoin that serves as a chiral auxiliary.

A short and efficient synthesis of (R)-(−)-sporochnol A in only five steps and 9% overall yield has been developed.Figure optionsDownload as PowerPoint slide

(2R,3R,1′R)-(+)-8-(1,5-Dimethyl-1-vinyl-4-hexenyl)-2,3-diphenyl-1,4-dioxaspiro[4.5]decan-8-olC30H38O3Ee = 98%[α]D20=+19.2 (c 0.6, CHCl3)Source of chirality: (R,R)-1,2-diphenyl ethanediolAbsolute configuration: (2R,3R,1′R)

(2R,3R,1′R)-(+)-8-(1,5-Dimethyl-1-vinyl-4-hexenyl)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-7-eneC30H36O2Ee = 98%[α]D20=+36.4 (c 1.0, CHCl3)Source of chirality: (R,R)-1,2-diphenyl ethanediolAbsolute configuration: (2R,3R,1′R)