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Updated: Jun 15, 2025
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Asymmetric synthesis of penostatins A-D from L-ascorbic acid
Maolin Wang1, Yuanliang Jia1, Folei Wu1
1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China. chenxc@scu.edu.cn.
Abstract:
The first asymmetric synthesis of (-)-penostatins B and D and the practical synthesis of (+)-penostatins A and C have been accomplished through a flexible strategy. The features of the synthesis are a BF3·OEt2-mediated Diels-Alder reaction of chiral dienophiles and methylcyclopentadienes with high chemo-, regio-, and stereoselectivity, followed by ozonolysis to install the common trisubstituted cyclopentane intermediate, and a hetero-Diels-Alder reaction with easily tunable facial selectivity, followed by sulfonate elimination to construct both enantiomeric tricyclic systems for penostatins A/C and B/D, respectively.
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