Abstract
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 photochemically promoted rearrangement of this last compound to the octahydro-1H-cyclobuta[e]indenone 13.
Original language | English |
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Pages (from-to) | 2078-2086 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 81 |
Issue number | 5 |
DOIs | |
Publication status | Published - 4 Mar 2016 |