Total synthesis of (+)-elacomine and (-)-isoelacomine, two hitherto unnamed oxindole alkaloids from Elaeagnus commutata

被引:95
作者
Pellegrini, C [1 ]
Weber, M [1 ]
Borschberg, HJ [1 ]
机构
[1] ETH ZENTRUM,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND
关键词
D O I
10.1002/hlca.19960790116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Racemic elacomine ((+/-)-2), a hemiterpene spiro oxindole alkaloid from Elaeagnus commutata, was synthesized in five steps from 6-methoxytryptamine (19) in 16% overall yield (Scheme 3). The final oxidative rearrangement of the corresponding beta-carboline precursor (+/-)-21 furnished isoelacomine ((+/-)-22) as a by-product (6% overall yield). A more elaborate route that started from L-tryptophan furnished (+)-2 and (-)-22 with optical purities of 76% (Scheme 4) and established the absolute configuration of these compounds. A reinvestigation of the alkaloidal content of the roots of E, commutata showed that both elacomine and isoelacomine occur naturally in racemic form.
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页码:151 / 168
页数:18
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