AI Article Synopsis
- The study presents a method for creating diverse benzannulated heterocycles (oxazepine, diazepine, thiazepine, etc.) using S-amino acids as starting materials.
- Key techniques include inter- and intramolecular Mitsunobu reactions, which help form various carbon-nitrogen, carbon-oxygen, and carbon-sulfur bonds.
- This work marks the first use of the Mitsunobu reaction to build seven- and eight-membered ring structures specifically from S-amino acids.
Article Abstract
The diversity-oriented organic synthesis of enantiomerically pure benzannulated oxazepine, diazepine, thiazepine, oxazocine, and diazocine scaffolds is described from easily accessible naturally occurring S-amino acids as chiral synthons. Inter- and intramolecular Mitsunobu reactions for the formation of carbon-nitrogen, carbon-oxygen, and carbon-sulfur bonds have been used as key transformations to construct these biologically important privileged heterocycles. This is the first example where the Mitsunobu approach has been utilized for the construction of S-amino acid based seven- and eight-membered ring systems.
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| http://dx.doi.org/10.1021/cc0601480 | DOI Listing |
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