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

Edward Prokof'evich Serebryakov 1
Edward Prokof'evich Serebryakov
, 
Galina Dmitrievna Gamalevich 1
Galina Dmitrievna Gamalevich
, 
Veacheslav N Kulcitki 2
Veacheslav N Kulcitki
, 
Nicon D Ungur 2
Nicon D Ungur
, 
Pavel Fedorovich Vlad 2
Pavel Fedorovich Vlad
10.1070/MC2002v012n02ABEH001566
Published 2002-04-30
Communication , Volume 12, Issue 2, 59-61
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Serebryakov E. P. et al. Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers // Mendeleev Communications. 2002. Vol. 12. No. 2. pp. 59-61.
GOST all authors (up to 50) Copy
Serebryakov E. P., Gamalevich G. D., Kulcitki V. N., Ungur N. D., Vlad P. F. Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers // Mendeleev Communications. 2002. Vol. 12. No. 2. pp. 59-61.
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TY - JOUR
DO - 10.1070/MC2002v012n02ABEH001566
UR - https://mendcomm.colab.ws/publications/10.1070/MC2002v012n02ABEH001566
TI - Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers
T2 - Mendeleev Communications
AU - Serebryakov, Edward Prokof'evich
AU - Gamalevich, Galina Dmitrievna
AU - Kulcitki, Veacheslav N
AU - Ungur, Nicon D
AU - Vlad, Pavel Fedorovich
PY - 2002
DA - 2002/04/30
PB - Mendeleev Communications
SP - 59-61
IS - 2
VL - 12
ER -
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@article{2002_Serebryakov,
author = {Edward Prokof'evich Serebryakov and Galina Dmitrievna Gamalevich and Veacheslav N Kulcitki and Nicon D Ungur and Pavel Fedorovich Vlad},
title = {Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers},
journal = {Mendeleev Communications},
year = {2002},
volume = {12},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2002v012n02ABEH001566},
number = {2},
pages = {59--61},
doi = {10.1070/MC2002v012n02ABEH001566}
}
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Serebryakov, Edward Prokof'evich, et al. “Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers.” Mendeleev Communications, vol. 12, no. 2, Apr. 2002, pp. 59-61. https://mendcomm.colab.ws/publications/10.1070/MC2002v012n02ABEH001566.

Abstract

(±)-α-Cyclogeraniol and (±)-drim-7-en-11-ol acetates obtained via the FSO3H-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 (5R,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,14R)-(−)-isoagath-12-en-15-ol of 69–80% ee in ∼3% yield.

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