Total synthesis of (+/-)-methyl rishirilide B.
[formula: see text] A regio- and stereospecific total synthesis of (+/-)-methyl rishirilide B (2b), and (alpha)2-macroglobulin inhibitor, is described. A key feature of the synthetic plan was regiospecific construction of a hydroanthracenone intermediate through condensation of a phenylsulfonyl isobenzofuranone with a functionalized 2-cyclohexen-1-one. Introduction of the vicinal trans-hydroxyl groups in the densely functionalized A-ring was accomplished via a novel one-pot procedure that involved oxidation of enolate anions with the Davis reagent.
Hauser
F M
FM
Department of Chemistry, State University of New York at Albany 12222, USA.
Xu
Y J
YJ
D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry*; D005343:Fibrinolytic Agents / Q000138:chemical synthesis*; D006868:Hydrolysis; D007202:Indicators and Reagents; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D000511:alpha-Macroglobulins / Q000037:antagonists & inhibitors*
D000873:Anthracenes; D005343:Fibrinolytic Agents; D007202:Indicators and Reagents; D000511:alpha-Macroglobulins; C410455:methyl rishirilide B; C043480:rishirilide B