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Chemoenzymatic Total Syntheses of Artonin I with an Intermolecular Diels?Alderase

Diels?Alder reaction is one of the most important transformations used in organic synthesis, with the ability to construct two new C?C bonds and up to four chiral centers simultaneously. However, the biggest synthetic challenge in Diels?Alder reaction lies in controlling its regio?, diastereo?, and enantioselectivity. Using Stille cross?coupling and enzymatic Diels?Alder reaction as the key steps, the first chemoenzymatic total synthesis of artonin I was achieved in 30% overall yield over only 7 steps. This enzymatic Diels?Alder reaction catalyzed by MaDA was featured with excellent endo? and enantioselectivity and high catalytic efficiency (kcat/KM = 362 ± 54 mM?1 s?1). These successful chemoenzymatic total syntheses of artonin I and dideoxyartonin I demonstrated the remarkable potential of the intermolecular Diels?Alderase MaDA in biocatalysis.This article is protected by copyright. All rights reserved

Publication date: 01/10/2020

Author: Xiaojing Liu, Jun Yang, Lei Gao, Liyun Zhang, Xiaoguang Lei

Reference: doi:10.1002/biot.202000119



This project has received funding from the European Union’s Horizon 2020 research and innovation programme under grant agreement No 870292.