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Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5-c]furans related to the tashironin class of sesquiterpenes

Sharma, Mukesh K.; Banwell, Martin; Willis, Anthony C.


The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the...[Show more]

CollectionsANU Research Publications
Date published: 2015-02-12
Type: Journal article
Source: The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00303


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