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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/d3ob00206c | DOI Listing |
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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