Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products

被引：4

作者：

Manchado, Alejandro ^{[1
]}

Elena Ramos, Victoria ^{[1
]}

Diez, David ^{[1
]}

Garrido, Narciso M. ^{[1
]}

机构：

[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, Plaza Caidos 1-5, Salamanca 37008, Spain

来源：

MOLECULES | 2020年 / 25卷 / 06期

关键词：

chiral lithium amide; asymmetric aza-Michael addition; asymmetric domino reaction; multicomponent reaction; cyclopentan[c]pyran; iridoid; nepetalactone; PURE LITHIUM AMIDES; CONJUGATE ADDITION; AMMONIA EQUIVALENTS; ENANTIOSELECTIVE SYNTHESIS; CLAISEN REARRANGEMENT; ESSENTIAL OIL; AMINO-ACIDS; SECOIRIDOIDS; GLYCOSIDES;

D O I：

10.3390/molecules25061308

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.

引用

页数：23

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