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Updated: Aug 25, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
First total synthesis of trans- and cis-resorcylide: remarkable hydrogen-bond-controlled, stereospecific ring-closing
Elias A Couladouros1, Anastasia P Mihou, Emmanuel A Bouzas
1Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, Athens, 118 55, Greece.
Abstract:
[reaction: see text] Stereospecific synthesis of the pair of natural macrolides, trans- and cis-resorcylide, was performed using ring-closing metathesis on dienes 3 and 4, which lack or feature an intramolecular H-bond, respectively. An effective Stille carbonylative coupling of benzyl chlorides 11 and 15 was employed for their preparation. The influence of intramolecular H-bonding on the interconversions of resorcylides was also studied.
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