Total Synthesis of rac-Keramamine C Enabled by Intrinsic H-Bond-Induced Conformational Fixation of Amides

Ganzmann J, Thurston R, Riester P, Hegmann N, Heinrich M (2026)

Publication Type: Journal article

Publication year: 2026

Journal

Article Number: e202501128

DOI: 10.1002/ejoc.202501128

Abstract

The manzamine alkaloid keramamine C contains a unique azacycloundecene subunit, which is constructed by ring-closing metathesis exploiting the intrinsic H-bond-induced conformational fixation of an amide bond. Taking advantage of this particular effect, the alkaloid could be prepared from readily available precursors in only five synthetic steps, where important further insight into the otherwise challenging ring-closing metathesis of 11-membered lactams was gained.

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How to cite

APA:

Ganzmann, J., Thurston, R., Riester, P., Hegmann, N., & Heinrich, M. (2026). Total Synthesis of rac-Keramamine C Enabled by Intrinsic H-Bond-Induced Conformational Fixation of Amides. European Journal of Organic Chemistry. https://doi.org/10.1002/ejoc.202501128

MLA:

Ganzmann, Jana, et al. "Total Synthesis of rac-Keramamine C Enabled by Intrinsic H-Bond-Induced Conformational Fixation of Amides." European Journal of Organic Chemistry (2026).

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