Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics

• Published in: Tetrahedron Vol. 56; no. 50; pp. 9781 - 9790
• Main Authors: Dougherty, Joseph M, Probst, Donald A, Robinson, Randall E, Moore, Joel D, Klein, Thomas A, Snelgrove, Kelley A, Hanson, Paul R
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 08-12-2000
• Subjects: cyclic sulfamides; metathesis; peptidomimetics; sulfur heterocycles; peptidomimetics; cyclic sulfamides; metathesis; sulfur heterocycles
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(00)00885-1

Ring-closing metathesis (RCM) strategies toward the synthesis of a number of constrained sulfamides are discussed. This approach exploits the inherent chemistry of sulfamides and sulfonyl carbamates to generate both symmetric and unsymmetric cyclic sulfamides. Two strategies are revealed, one centers on the RCM reaction of allylated sulfamides
9a–
e to generate the
C
2-symmetric cyclic sulfamides
4a–
e in high yields. A second RCM strategy utilizes the known sulfonyl carbamate
15 to prepare unsymmetric cyclic sulfamides
16 and
6 in two four-step sequences. Overall, the routes described are applicable to the synthesis of a variety of constrained dipeptidal sulfamides representing novel peptidomimetic scaffolds.