Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides

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• 作者：Mikio Fujii ; Motonori Fukumura ; Yumiko Hori ; Yasuaki Hirai ; Hiroyuki Akita ; Kaoru Nakamura ; Kazuo Toriizuka and Yoshiteru Ida
• 刊名：Tetrahedron: Asymmetry
• 出版年：2006
• 出版时间：11 September 2006
• 年：2006
• 卷：17
• 期：15
• 页码：2292-2298
• 全文大小：170 K

文摘

rac-Hept-1-en-3-ol 4 was subjected to an enantioselective esterification in the presence of Novozyme 435 and vinyl crotonate as the acyl donor to give (3S)-oct-1-en-3-yl crotonate 7 in >99 % ee and (3R)-alcohol 4 in 99 % ee. The E-value of this enzymatic reaction was found to be >1000. The (S)-crotonic ester 7 was converted by ring-closing metathesis (RCM) using Grubbs’ catalyst to give (S)-oct-2-en-4-olide 1 in 96 % yield while keeping the high enantiomeric excess.