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Org Lett. 2010 Apr 2;12(7):1600-3. doi: 10.1021/ol100333d.

Synthesis of the spiroiminal moiety of marineosins A and B.

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1
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.

Abstract

A model for the spiroiminal moiety of marineosins A and B was prepared starting from methylvalerolactone. Addition of vinylmagnesium bromide, protection of the alcohol, and reaction of the vinyl ketone with a protected pyrrole-2-carbonitrile N-oxide gave an isoxazoline. Hydrogenolysis of the N-O bond with Raney nickel gave a keto imine that cyclized to a hemi-iminal. O-Methylation, acid-catalyzed cleavage of the TES group and spiroiminal formation, and deprotection completed a seven-step synthesis.

PMID:
20218641
PMCID:
PMC2877921
DOI:
10.1021/ol100333d
[Indexed for MEDLINE]
Free PMC Article
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