Synthesis studies on the Melodinus alkaloid meloscine

Ken S. Feldman; Joshua F. Antoline

doi:10.1016/j.tet.2012.12.032

Synthesis studies on the Melodinus alkaloid meloscine

Ken S. Feldman, Joshua F. Antoline

Chemistry

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1434-1445
Number of pages	12
Journal	Tetrahedron
Volume	69
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2012.12.032
State	Published - Feb 4 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.12.032

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title = "Synthesis studies on the Melodinus alkaloid meloscine",

abstract = "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.",

author = "Feldman, {Ken S.} and Antoline, {Joshua F.}",

note = "Funding Information: We thank the National Institutes of Health, General Medical Sciences ( GM 72572 ) for support of this work. The X-ray facility is supported by NSF CHE 0131112.",

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AU - Antoline, Joshua F.

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AB - 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.

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Synthesis studies on the Melodinus alkaloid meloscine

Abstract

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