Efficient and Selective Syntheses of (all-E)- and (6E,10Z)-2′-O-Methylmyxalamides D via Pd-Catalyzed Alkenylation−Carbonyl Olefination Synergy
- 2 July 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (15) , 3223-3226
- https://doi.org/10.1021/ol801115s
Abstract
Highly efficient and selective syntheses of both (all-E) and (6E,10Z)-isomers of 2′-O-methylmyxalamide D (2 and 3), in which the crucial conjugated pentaene moieties were assembled in ≥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.Keywords
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