通过Pauson-Khand反应从碳水化合物合成环烯醚萜：从D-葡糖醛衍生合成高级高氧化态环戊烷并环吡喃糖苷
Iridoids from Carbohydrates via Pauson-Khand Reaction: Synthesis of Advanced Highly Oxygenated Cyclopentane-Annulated Pyranosides from D-Glucal Derivatives.
作者信息
Marco-Contelles José, Ruiz-Caro Juliana
机构信息
Instituto de Química Orgánica General (CSIC), Laboratorio de Radicales Libres, C/Juan de la Cierva, 3; 28006-Madrid, Spain.
出版信息
J Org Chem. 1999 Oct 29;64(22):8302-8310. doi: 10.1021/jo991044x.
PMID:11674752
Abstract
The Pauson-Khand reaction on suitable 4-oxa-hept-1-en-6-ynes (1, 17) obtained from 3,4,6-tri-O-acetyl-D-glucal gives the cyclopentane-annulated pyranosides (2, 18) that can be efficiently and stereoselectivelly transformed into chiral, advanced, highly oxygenated intermediates (10, 16, 24) for the synthesis of iridoid aglycones.
摘要
对由3,4,6-三-O-乙酰基-D-葡萄糖烯得到的合适的4-氧杂-庚-1-烯-6-炔（1, 17）进行Pauson-Khand反应，得到环戊烷稠合的吡喃糖苷（2, 18），其可高效且立体选择性地转化为用于合成环烯醚萜苷元的手性、高级、高度氧化的中间体（10, 16, 24）。
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