Details

Autor(en) / Beteiligte

• Serebryakov, Edward P.
• Gamalevich, Galina D.
• Kulcitki, Veacheslav N.
• Ungur, Nicon D.
• Vlad, Pavel F.

Titel

Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers

Ist Teil von

• Mendeleev communications, 2002, Vol.12 (2), p.59-60

Ort / Verlag

Elsevier B.V

Erscheinungsjahr

2002

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• (±)-α-Cyclogeraniol and (±)-drim-7-en-11-ol acetates obtained via the FSO 3H-induced cyclisation of geraniol and ( E)-farnesol and subsequent acetylation were hydrolysed in the presence of hog pancreas lipase (PPL) to afford ( R)-(+)-α-cyclogeraniol (ee ∼30% at the optimal conversion C = 20±2%) and (5 R,9R,10R)-(+)-drim-7-en-11-ol ( ee 78.5% at C = 30%), respectively; (±)-15-acetoxyisoagath-12-ene, obtained similarly from all- E-geranylgeraniol, is resistant to PPL-mediated hydrolysis, but is hydrolysed in the presence of lipase from Candida cylindracea to afford (10S,14 R)-(−)-isoagath-12-en-15-ol of 69–80% ee in ∼3% yield.