First total synthesis of a new pyrrolizidine alkaloid, amphorogynine A

First total synthesis of a new pyrrolizidine alkaloid, amphorogynine A
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DOI:
10.1016/s0040-4039(03)00070-4
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发表时间:
2003-02-17
影响因子:
1.8
通讯作者:
Takabe, K
Takabe, K
中科院分区:
化学4区
文献类型:
--
作者:
Yoda, H;Egawa, T;Takabe, K

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本文报道了一种新型吡咯利西啶类生物碱两性花碱a及其1-外显异构体的首次不对称合成方法。关键的2,4-二取代吡咯烷环是由手性内酰胺衍生物结合d-苹果酸衍生的骨架,通过不对称顺性烯丙基化的功能化的烯丙基化构建的。2003爱思唯尔科学有限公司版权所有。
An efficient and stereodefined strategy is described for the first asymmetric synthesis of a new type of pyrrolizidine alkaloids, amphorogynine A and its 1-epi-isomer. The key 2,4-disubstituted pyrrolidine ring was constructed by elaboration of the chiral lactam derivative incorporating the D-malic acid-derived skeleton through asymmetric cis-allylation of the functionalized allysilane. (C) 2003 Elsevier Science Ltd. All rights reserved.