Allenyl azide cycloaddition chemistry: Application to the total synthesis of (±)-meloscine

Ken S. Feldman; Joshua F. Antoline

doi:10.1021/ol203463n

Allenyl azide cycloaddition chemistry: Application to the total synthesis of (±)-meloscine

Ken S. Feldman, Joshua F. Antoline

Chemistry

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

32 Scopus citations

Abstract

The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

Original language	English (US)
Pages (from-to)	934-937
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	3
DOIs	https://doi.org/10.1021/ol203463n
State	Published - Feb 3 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol203463n

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title = "Allenyl azide cycloaddition chemistry: Application to the total synthesis of (±)-meloscine",

abstract = "The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.",

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AU - Antoline, Joshua F.

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N2 - The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

AB - The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

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Allenyl azide cycloaddition chemistry: Application to the total synthesis of (±)-meloscine

Abstract

All Science Journal Classification (ASJC) codes

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