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Synthesis of fused pyrrolines by the intramolecular cycloadition of azides application to the pyrrolizidine alkaloids.

✍ Scribed by William H. Pearson

Book ID: 104222374
Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 280 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89182-0

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✦ Synopsis

Intramolecular 1,3-dipolar cycloaddition of azide 4 proceeds through triazoline 5 and vinyl aziridine 6, resulting in the formation of the 1,5-homodienyl shift product 7 and the tetrahydropyrrolizines 8 and 9. Compound 8 represents a formal total synthesis of suprnidine.

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