Cryptocaryolone diacetate

An (E)-selective CM reaction with an acrylate (Scheme 61) was applied by Smith and O Doherty in the enantioselective synthesis of three natural products with cyclooxygenase inhibitory activity (cryptocarya triacetate (312), cryptocaryolone (313), and cryptocaryolone diacetate (314)) [142]. CM reaction of homoallylic alcohol 309 with ethyl acrylate mediated by catalyst C led (E)-selectively to d-hydroxy enoate 310 in near quantitative yield. Subsequent Evans acetal-forming reaction of 310, which required the trans double bond in 310 to prevent lactonization, led to key intermediate 311 that was converted to 312-314. 

Wang, X., Wang, W, Zheng, H., Su, Y., Jiang, T., He, Y, She, X. (2009). Efficient asymmetric total syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate. Organic Letters, 11, 3136-3138. 

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