An Ireland-Claisen approach to lignans: synthesis of the putative structure of 5-epi-eupomatilone-6.
A novel Ireland-Claisen approach to the putative structure of eupomatilone-6 is described. The rearrangement established the C3 and C4 stereocenters and concomitantly generated a vinyl epoxide. The C5 oxygen was installed by cyclization of the pentenoic acid carboxyl group onto the vinyl epoxide in an S(N)2' fashion to afford the C5-epi stereochemistry. The natural C5 stereochemistry was accessed via a substrate directed dihydroxylation.
Hutchison
John M
JM
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
Hong
Sang-Phyo
SP
McIntosh
Matthias C
MC
D019380:Anti-HIV Agents / Q000737:chemistry; D000935:Antifungal Agents / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry
D019380:Anti-HIV Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001572:Benzofurans; D017705:Lignans; C485126:eupomatilone-6