Work

Total Syntheses of (±)-Massadine and Massadine Chloride

Year: 2008

Type: article

Abstract: The total syntheses of the complex pyrrole−imidazole alkaloids (±)−massadine and (±)−massadine chloride is described using a carefully orchestrated sequence of manipulations on highly polar and structurally complex intermediates. Key to the completion of this synthetic endeavor was the exploration of a unique and chemoselective method to oxidize unprotected guanidines under aqueous conditions in air. This oxidation has been optimized and applied to a selection of spirocyclic guanidines of varying complexity. Additionally, the 3,7- epi analogues of these interesting natural products have been synthesized and fully characterized.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja8074852

Authors: Shun Su, Ian B. Seiple, Ian S. Young, Phil S. Baran

Institution: Scripps Research Institute

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Economic and Social Research Council, National Institute of General Medical Sciences

Awards: G4190247771, The Centre of Excellence for Public Health (Northern Ireland), Synthesis of Pyrrole-Imidazole Alkaloids, G963544812