Total synthesis of varitriol, varioxirane, and enantiomer of the proposed biosynthetic precursor.
The first stereoselective total synthesis of varioxirane was accomplished, and the proposed biosynthetic pathway was supported by converting varioxirane to (+)-varitriol. The first total synthesis of enantiomer of the proposed biosynthetic precursor, (1E,3S,4R,5E)-1-(2-(hydroxymethyl)-3-methoxyphenyl)hepta-1,5-diene-3,4-diol, was also achieved by utilizing the unreacted allylic alcohol obtained during the Sharpless kinetic resolution step. Other key steps include the Horner-Wadsworth-Emmons reaction and the diastereoselective reduction of α,β-unsaturated ketone to its corresponding alcohol.
Division of CPC (Organic Chemistry-II), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. gsudhakar@iict.res.in
Gangarajula
G
Sudhakar
Jakka
J
Raghavaiah
D001592:Benzyl Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D001592:Benzyl Alcohols; D005663:Furans; C456048:varioxirane; C456047:varitriol