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学科主题: 天然产物有机化学
题名: Synthesis of natural fragrant molecules cis-3-methyl-4-decanolide and aerangis lactone. General enantioselective routes to β,γ,-cis-Disubstituted γ-Lactones and γ,δ-cis-disubstituted δ-Lactones.
其他题名: 天然芳香分子顺式-3-甲基-类癸醇及Aerangis内酯,合成β,γ-顺式双取代丁内酯及β,δ-顺式双取代戊内酯的对映体选择性合成通用方法
作者: 伍贻康 ; 沈鑫 ; 唐朝军 ; 陈志龙 ; 胡祺 ; 施伟
通讯作者: 伍贻康
刊名: J. Org. Chem.
发表日期: 2002-01-01
卷: 67, 期:11, 页:3802-3810
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机化学实验室
英文摘要: Ceneral enantioselective routes to 3,4-cis-dialkyl substituted γ-lactones and 4,5-cis-dialkyl substituted δ-lactones using TiCl^4-mediated evans asymmetric aldolization as the key step are reported. The synthesese are exemlified with two natural fragrant molecules, cis-3-methyl-4-decanolide (1) and aerangis lactone (2). The (R,R)steroegenic centers were established using (S)-phenylalanine-derived 2-oxazolidinone or thiazolidinethione as chiral auxiliary, whereas the (S,S) ones were constructed with auxiliary prepared from (R)-phenylglycine. NaBH^4/CaCl^2/THF in the presence of a small amount of EtOH was introduced as a new effective method for reductive cleavage of chiral oxazolidinone auxiliaries. Previously unknown, tricky concentration effects were observed during the monotosylation of diol 7 and BOM protection of Evans aldol 23.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20305
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
伍贻康,沈鑫,唐朝军,等. Synthesis of natural fragrant molecules cis-3-methyl-4-decanolide and aerangis lactone. General enantioselective routes to β,γ,-cis-Disubstituted γ-Lactones and γ,δ-cis-disubstituted δ-Lactones.[J]. J. Org. Chem.,2002,67(11):3802-3810.
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