Total Synthesis of (+)-ent-Cyclizidine: Absolute Configurational Confirmation of Antibiotic M146791
Organic Letters2011Vol. 13(5), pp. 1048–1051
Citations Over TimeTop 25% of 2011 papers
Abstract
The first total synthesis of the enantiomer of the indolizidine alkaloid, cyclizidine, was accomplished from readily available d-serine as the starting chiron. The relevant key reactions involve the stereocontrolled construction of the indolizidine ring system with the required functionality and further elaboration to install the cyclopropyl dienyl side chain. With this total synthesis, the absolute configuration of the natural product based on a redetermination of its X-ray structure has been confirmed.
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