Journal
TETRAHEDRON
Volume 69, Issue 5, Pages 1434-1445Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.12.032
Keywords
Alkaloid; Meloscine; Allenyl azide cycloaddition
Categories
Funding
- National Institutes of Health, General Medical Sciences [GM 72572]
- NSF [CHE 0131112]
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The pentacyclic Melodinus alkaloid (+/-)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring-closing metathesis to forge the tetrahydropyridine ring. (C) 2012 Elsevier Ltd. All rights reserved.
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