Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy.
Highly efficient and selective syntheses of both (all- E) and (6 E,10 Z)-isomers of 2'- O-methylmyxalamide D ( 2 and 3), in which the crucial conjugated pentaene moieties were assembled in > or =98% stereoselectivity through the use of two Pd-catalyzed alkenylation reactions, the Horner-Wadsworth-Emmons (HWE) olefination, and either the Corey-Schlessinger-Mills modified (CSM-modified) Peterson olefination for 2 or the Still-Gennari olefination for 3, are reported. Either 2 or 3 was prepared in 16% yield in seven steps from propargyl alcohol.
Wang
Guangwei
G
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Huang
Zhihong
Z
Negishi
Ei-Ichi
E
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
C511236:2'-O-methylmyxalamide D; D000475:Alkenes; D011090:Polyenes; D010165:Palladium