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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.

Citation

Miriam Ruiz, Pilar López-Alvarado, J Carlos Menéndez. Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process. Organic & biomolecular chemistry. 2010 Oct 21;8(20):4521-3

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PMID: 20717611

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