681029-66-3Relevant academic research and scientific papers
Asymmetric aldol reactions using catalytic D(+)-proline: A new, economic and practical approach to a commonly employed C1-C6 keto-acid synthon of the epothilones
Zheng, Yansong,Avery, Mitchell A.
, p. 2091 - 2095 (2007/10/03)
A new approach to ketoacid 4, a common C1-C6 fragment used in the total synthesis of epothilones was initiated by direct aldol reaction of acetone with a pivaldehyde-like substance 5, catalyzed with D-proline, leading to a 2,6-diketoalcohol with better than 99% ee. Further intramolecular closure of the diketone 8 followed by oxidation of the silyl protected hydroxycyclohexenone 14 led to the desired product 4. None of the steps have been optimized, yet the overall yield for the four-step process is 31%. The use of commercially available D-proline to construct the chiral center of 4 under very mild reaction conditions provided an economical and practical method for its construction.
