Total synthesis of N-methylwelwitindolinone D isonitrile
Vikram Bhat1, Kevin M Allan, Viresh H Rawal
1Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, United States.
None:
Described is a concise total synthesis of N-methylwelwitindolinone D isonitrile, the first in a family of complex bicyclo[4.3.1]decane-containing indole alkaloids to yield to synthesis. The complete carbon core of the natural product was assembled rapidly through a Lewis acid-mediated alkylative coupling followed directly by a palladium-catalyzed enolate arylation reaction. The final ring of the pentacycle was introduced by an indole oxidation/cyclization, and the isonitrile was installed through the rearrangement of an aldehyde to an isothiocyanate followed by desulfurization.
Related Concept Videos
Nitrosation of Enols
Preparation of Nitriles
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard reagent...
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...


