2-甲酰基吡咯生物碱萱草胺 I 的全合成和立体化学修订。

Total Synthesis and Stereochemical Revision of the 2-Formylpyrrole Alkaloid Hemerocallisamine I.

机构信息

School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1142, New Zealand.

Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , Private Bag 92019, Auckland 1142, New Zealand.

出版信息

J Nat Prod. 2017 Jun 23;80(6):1926-1929. doi: 10.1021/acs.jnatprod.7b00314. Epub 2017 Jun 7.

DOI:10.1021/acs.jnatprod.7b00314

PMID:28590122

Abstract

The first total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is reported. The convergent synthesis features a key Maillard-type condensation of a complex amine derived from cis-4-hydroxy-l-proline with a dihydropyranone, to directly furnish the 2-formylpyrrole ring system. The absolute configuration of hemerocallisamine I has been revised on the basis of optical rotation data obtained for the synthesized compound.

摘要

首次报道了 2-甲酰基吡咯生物碱萱草胺 I 的全合成。该收敛性合成的关键步骤是顺式-4-羟基-L-脯氨酸衍生的复杂胺与二氢吡喃酮之间的 Maillard 型缩合，直接构建 2-甲酰基吡咯环系统。基于合成化合物的旋光数据，对萱草胺 I 的绝对构型进行了修订。