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Chemoenzymatic Total Syntheses of Artonin I with an Intermolecular Diels–Alderase
Author(s) -
Liu Xiaojing,
Yang Jun,
Gao Lei,
Zhang Liyun,
Lei Xiaoguang
Publication year - 2020
Publication title -
biotechnology journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.144
H-Index - 84
eISSN - 1860-7314
pISSN - 1860-6768
DOI - 10.1002/biot.202000119
Subject(s) - biocatalysis , stille reaction , total synthesis , intermolecular force , chemistry , yield (engineering) , catalysis , stereochemistry , diels–alder reaction , combinatorial chemistry , organic chemistry , reaction mechanism , molecule , materials science , metallurgy
Diels–Alder reaction is one of the most important transformations used in organic synthesis, with the ability to construct two new CC 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 is achieved in 30% overall yield over only seven steps. This enzymatic Diels–Alder reaction catalyzed by MaDA is featured with excellent endo‐ and enantioselectivity and high catalytic efficiency ( k cat / K M = 362 ± 54 m m −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.