Total Synthesis of -Patulolide

Abstracted with permission from Heterocycles, 1994,39, 67 1994 The Japan Institute of Heterocyclic Chemistry 

Abstracted with permission from J. Org. Chem., 1995,60, 276 1995 American Chemical Society 

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This method was successfully used in a concise catalytic enantioselective total synthesis of (+)-patulolide C by serving as a key asymmetric C—O bond formation step (Scheme 5.33)." ... 

The lanthanide (or yttrium)-lithium heterobimetallic complexes, LnLB was found to promote catalytic asymmetric cyano-ethoxycarbonylation reaction and cyano-phosphorylation reaction of aldehydes [164]. In these reactions, H2O, BuLi, and Ar3P(0) (Ar = 2,6-dimethoxyphenyl) were essential to achieve high enantioselectivity as well as good reactivity (Scheme 13.53). A total synthesis of patulolide C was achieved using the catalytic asymmetric cyano-ethoxycarbonylation reaction... 

Thijs, L., Egenberger, D. M., Zwanenburg, B. An enantioselective total synthesis of the macrolide patulolide C. Tetrahedron Lett. 1989, 30, 2153-2156. 

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