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(+)-异阿魏内酯、(+)-海绵酮-16-酮和 3-去氧恰瓦酮 A 的酶促全合成——一种生物催化的多烯环化反应。

Chemoenzymatic synthesis of (+)-isoagatholactone, (+)-spongian-16-one, and 3-deoxychavalone A biocatalytic polyene cyclization.

机构信息

State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.

出版信息

Org Biomol Chem. 2023 Jul 12;21(27):5527-5531. doi: 10.1039/d3ob00206c.

Abstract

The stereoselective cyclization of geranylgeraniol catalysed by squalene-hopene cyclase (SHC) was investigated. By use of this transformation, spongiane diterpenoids (+)-isoagatholactone and (+)-spongian-16-one, and meroterpenoid 3-deoxychavalone A were synthesized in a concise and redox-economic manner. This work showcases the application of SHC-catalysed cyclization as a key step in terpenoid synthesis.

摘要

研究了鲨烯-角鲨烯环化酶(SHC)催化的香叶基香叶醇的立体选择性环化。通过这种转化,以简洁和氧化还原经济的方式合成了海绵二萜类化合物(+)-异阿魏酸内酯和(+)-海绵-16-酮,以及美罗萜 3-去氧查尔酮 A。这项工作展示了 SHC 催化的环化在萜类合成中的关键步骤的应用。

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