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Structure revision and syntheses of epohelmins A and B
Journal article   Peer reviewed

Structure revision and syntheses of epohelmins A and B

Barry B Snider and Xiaolei Gao
Organic Letters, Vol.7(20), pp.4419-4422
09/01/2005
PMID: 16178548

Abstract

Cyclization Magnetic Resonance Spectroscopy Oxidation-Reduction Stereoisomerism Bridged Bicyclo Compounds, Heterocyclic - chemistry Molecular Structure Bridged Bicyclo Compounds, Heterocyclic - metabolism Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Epohelmins A (24) and B (26) have been reassigned as pyrrolizidin-1-ols, rather than the proposed 9-oxa-4-azabicyclo[6.1.0]nonane structures 1 and 2, respectively. Syntheses of epohelmin A (24) (eight steps, 52% overall yield) and epohelmin B (26) (11 steps, 43% overall yield) have been achieved starting from N-Cbz-(S)-prolinal (9) and ortho ester ketone 17 using a stereoselective aldol reaction and a stereoselective reductive cyclization as the key steps.

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