A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.
[reaction: see text] A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.
Bertrand
Myra Beaudoin
MB
Department of Chemistry, University of Michigan, Ann Arbor, 48109-1055, USA.
Wolfe
John P
JP
D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D001230:Aspergillus / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D000970:Antineoplastic Agents; C058280:preussin; D010165:Palladium; D000841:Anisomycin