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Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process†
Miriam Ruiz,Pilar López-Alvarado,J. Carlos Menéndez
Organic & Biomolecular Chemistry Pub Date : 08/18/2010 00:00:00 , DOI:10.1039/C0OB00382D
Abstract

An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing the most efficient synthesis of the welwistatin core to date, this method has the advantage of installing an oxygenated function at the welwistatin D ring.

Graphical abstract: Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process
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