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Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol

Chang, Ee Ling; Bolte, Benoit; Lan, Ping; Willis, Anthony; Banwell, Martin


Chemoenzymatic and stereoselective total syntheses of the non-natural enantiomeric forms of the recently isolated protoilludane natural products 8-deoxydihydrotsugicoline (1) and radudiol (2) (viz. ent-1 and ent-2, respectively) are reported. The key steps involve the Diels-Alder cycloaddition of cyclopent-2-en-1-one to the acetonide derived from enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 3, elaboration of the resulting adduct to the tricyclic ketone 12, and a...[Show more]

CollectionsANU Research Publications
Date published: 2016-03-04
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.6b00043
Access Rights: Open Access


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