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Total Synthesis of (-)-Curvulamine.

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Curvulamine and related polypyrrole alkaloids represent a fascinating new class of natural products with unprecedented chemical structures, intriguing biological activities, and mysterious biosynthetic origins. Herein we report the first studies… Click to show full abstract

Curvulamine and related polypyrrole alkaloids represent a fascinating new class of natural products with unprecedented chemical structures, intriguing biological activities, and mysterious biosynthetic origins. Herein we report the first studies towards these molecules, resulting in a 10-step total synthesis of (-)-curvulamine, a dimeric member with promising Gram-positive and -negative antibiotic activity. A number of interesting chemical findings, including exploitation of the heteroaromatic pyrrolo[1,2-a]azepinone nucleus and an efficient stereodivergent reduction, are reported.

Keywords: total synthesis; synthesis curvulamine; curvulamine

Journal Title: Journal of the American Chemical Society
Year Published: 2020

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