SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE
SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE
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DOI：
10.1021/ja00009a043
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发表时间：
1991-04-24
影响因子：
15
通讯作者：
ZASLONA, A
中科院分区：
文献类型：
--
作者：
JEFFORD, CW;TANG, Q;ZASLONA, A
本文报道了（-）-中氮茚167 B（1）和（+）-单吗啉（2）的对映体合成。 D-正缬氨酸和L-丙氨酸通过与2，5-二甲氧基四氢呋喃反应转化为它们的1-吡咯衍生物。此后，N-链烷酸取代基的Arndive-Eistert同系化，然后乙酸铑（II）催化分解其α-重氮酮衍生物，提供相关的双环前体，其固有的手性指导催化加氢，得到1和2。 提供5-丁基 2中的侧链是通过由丁酰氯和L-丙氨酸的吡咯类似物获得的混合酸酐的现有刘易斯酸催化重排制备的。
The enantiogenic syntheses of (-)-indolizidine 167B (1) and (+)-monomorine (2) are described. D-Norvaline and L-alanine are converted into their 1-pyrrole derivatives by reaction with 2,5-dimethoxytetrahydrofuran. Thereafter, Arndt-Eistert homologation of the N-alkanoic acid substituent, followed by rhodium(II) acetate catalyzed decomposition of its alpha-diazo ketone derivative, provides the relevant bicyclic precursors, the vested chirality of which directs catalytic hydrogenation affording 1 and 2. Provision for the 5-butyl side chain in 2 is made by prior Lewis acid catalyzed rearrangement of the mixed anhydride obtained from butyryl chloride and the pyrrole analogue of L-alanine.