Asymmetric Synthesis of Apratoxin E

作者:Mao Zhuo Ya; Si Chang Mei; Liu Yi Wen; Dong Han Qing; Wei Bang Guo*; Lin Guo Qiang
来源:Journal of Organic Chemistry, 2016, 81(20): 9903-9911.
DOI:10.1021/acs.joc.6b02086

摘要

An efficient method for asymmetric synthesis of apratoxin E 2 is described in this report. The chiral lactone 8, recycled from the degradation of saponin glycosides, was utilized to prepare the non-peptide fragment 6. In addition to this "from nature to nature" strategy, olefin cross-metathesis (CM) was applied as an alternative approach for the formation of the double bond. Moreover, pentafluorophenyl diphenylphosphinate was found to be an efficient condensation reagent for the macrocyclization.