Chinese Journal of Organic Chemistry >
Synthesis of Right Segment of Ingramycin
Received date: 2013-07-06
Revised date: 2013-07-27
Online published: 2013-08-13
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372205)
The right segment of ingramycin contains a synthesis-challenging chiral tertiary alcohol structural motif. Based on methodology developed on our laboratory to construct chiral tertiary alcohols via[2,3]-Meisenheimer rearrangement, the synthesis of right segment of ingramycin was successfully achieved over fifteen steps via successive Wittig reaction,[2,3]-Meisenheimer rearrangement, selective ester group reduction with NaBH4, and etc. The total yield was 28% and ee value was 90%.
Gao Kaige , Sun Moran , Zhu Ming , Zhou Hang , Cao Qiwei , Yang Hua . Synthesis of Right Segment of Ingramycin[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 1939 -1944 . DOI: 10.6023/cjoc201307011
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