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

Org Biomol Chem

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.

Published: July 2023


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Article 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.

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http://dx.doi.org/10.1039/d3ob00206cDOI Listing

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

Org Biomol Chem

July 2023

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.

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.

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