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Tandem ring-closing metathesis/isomerization reactions for the total synthesis of violacein.

Organic letters (2013-04-05)
Mette T Petersen, Thomas E Nielsen
ABSTRACT

A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ruthenium, powder, 99.99% trace metals basis
Sigma-Aldrich
Ruthenium, powder, −200 mesh, 99.9% trace metals basis
Sigma-Aldrich
Ruthenium, sponge, −100 mesh, 99.9% trace metals basis
Sigma-Aldrich
Violacein from Janthinobacterium lividum, >98% (violacein (minimum 85% violacein) and deoxyviolacein, HPLC)
Sigma-Aldrich
Ruthenium black