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

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https://figshare.com/articles/dataset/Chemoenzymatic_Total_Syntheses_of_the_Enantiomers_of_the_Protoilludanes_8_Deoxydihydrotsugicoline_and_Radudiol/2304355
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资源简介:
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.
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2016-02-29
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