The first synthesis of marinopyrrole B, which is highly active against methicillin-resistant Staphylococcus aureus, is described. The route involved constructing a pyrrole ring on the nitrogen of a 3-bromo-4,5-dichloropyrrole by N-alkylation with a special Michael acceptor having an allylic leaving group; the second pyrrole ring was then formed by a Paal-Knorr reaction.
Selenium-stabilized carbanions are available by a route that does not involve acid-catalyzed formation of selenoacetals. Aldehydes are converted first into alpha-hydroxystannanes and then into alpha-(phenylseleno)stannanes. Treatment with BuLi affords selenium-stabilized carbanions by preferential Sn/Li exchange.
Organo-selenium compounds S 0130 [1-(Phenylseleno)alkyl]stannanes -Mixed Selenium/Tin Analogues of Acetals: Preparation from α-Hydroxystannanes and Use for Generating Selenium-Stabilized Carbanions. -The mixed selenoacetals (V) smoothly react with BuLi to afford selenium-stabilized carbanions. Treatment of the latter with aldehydes provides hydroxyselenides as useful synthons. They can easily be converted into diverse allylic alcohols. -(FERNANDOPULLE, S. C.; CLIVE*, D. L. J.; YU, M.; J. Org. Chem. 73 (2008) 15, 6018-6021; Dep. Chem., Univ. Alberta, Edmonton, Alberta T6G 2G2, Can.; Eng.) -Jannicke 50-180
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