Аннотация:
(±)-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.
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
E. P. Serebryakov, G. D. Gamalevich, V. N. Kulcitki, N. D. Ungur, P. F. Vlad, “Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers”, Mendeleev Commun., 12:2 (2002), 59–61
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https://www.mathnet.ru/rus/mendc4091
https://www.mathnet.ru/rus/mendc/v12/i2/p59
Эта публикация цитируется в следующих 6 статьяx:
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James R. Annand, Paul S. Riehl, Danielle M. Schultz, Corinna S. Schindler, “High-Throughput Approach toward the Development of a Mizoroki–Heck Reaction To Access Tricyclic Spirolactones”, J. Org. Chem., 85:14 (2020), 9071
Stefano Serra, Omar Piccioni, “A new chemo-enzymatic approach to the stereoselective synthesis of the flavors tetrahydroactinidiolide and dihydroactinidiolide”, Tetrahedron: Asymmetry, 26:10-11 (2015), 584
Stefano Serra, Francesco G. Gatti, Claudio Fuganti, “Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol”, Tetrahedron: Asymmetry, 20:11 (2009), 1319
Veaceslav Kulciţki, Marina Grinco, Pavel Vlad, Nicon Ungur, “Electrophilic Cyclization of Diterpenoids”, ChemJMold, 1:1 (2006), 22
Edward P. Serebryakov, Galina D. Gamalevich, Veacheslav N. Kulcitki, Nicon D. Ungur, Pavel F. Vlad, “Superacidic Cyclization—Lipase‐Mediated Kinetic Resolution as a Short Route from Achiral Linear Isoprenoid Alcohols to Scalemic Cyclic Isomers.”, ChemInform, 33:38 (2002), 186
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