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

Year: 2026

Type: article

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.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202501128

Authors: Jana Ganzmann, Ryan Thurston, Pascal Riester, Nina Hegmann, Markus R. Heinrich

Institution: Friedrich-Alexander-Universität Erlangen-Nürnberg

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

OpenAlex ID: W7142056529

FWCI:

Cites: 39

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