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Synfacts 2012; 8(4): 0349
DOI: 10.1055/s-0031-1290567
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Meloscine

Contributor(s):
Steven V. Ley
,
Catherine F. Carter
Feldman KS, * Antoline JF. The Pennsylvania State University, University Park, USA
Allenyl Azide Cycloaddition Chemistry: Application to the Total Synthesis of (±)-Meloscine.

Org. Lett. 2012;
14: 934-937
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Further Information

Publication History

Publication Date:
20 March 2012 (online)

 
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Key words

(±)-meloscine - allenyl azide cycloaddition - diradical cyclization cascade - ring-closing metathesis

Significance

(±)-Meloscine is a Melodinus alkaloid containing an azabicyclo[3.3.0]octane core within a pentacyclic framework. The total synthesis was achieved here in 19 steps from 2-bromobenzaldehyde.


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Comment

Bicycle J was formed by a key allenyl azide cyclization cascade involving loss of nitrogen and a diradical recombination in I to construct a C–C bond. The final ring was synthesized using ring-closing metathesis.


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