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ABC → ABCE/D Based Approaches to the Pentacyclic Ring System of the Vinca Alkaloids Using Intramolecular Hetero-[2+2]cycloaddition and Gold(I)-Catalyzed 6-endo-dig Cyclisation Protocols

G. Banwell, Martin; V. White, Lorenzo; C. Willis, Anthony


The angularly substituted tetrahydrocarbazole 13, which is readily obtained from cyclohexane-1,4-dione monoethylene ketal (6) using Fischer indole chemistry, has been converted into the isothiocyanate 16. Photolysis of this last compound affords, via an intramolecular hetero-[2+2]cycloaddition reaction, the pentacyclic "-thiolactam 17 that incorporates the ABCE ring substructure of natural products 1-3. Attempts to effect a two-carbon homologation of the four-membered ring within compound 17,...[Show more]

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
DOI: 10.3987/COM-14-S(K)19


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