Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides

作者：Qi, Na; Allu, Srinivasa Rao; Wang, Zhanlong; Liu, Qang; Guo, Jian^*; He, Yun^*

来源：Organic Letters, 2016, 18(18): 4718-4721.

DOI：10.1021/acs.orglett.6b02371

• ENANTIOSELECTIVE SYNTHESIS
• STILLE REACTION
• DEPSIPEPTIDES

The concise total syntheses of the potent HIV inhibitors aetheramides A and B (IC50 values of 15 and 18 nM), as well as three pairs of their stereoisomers, were achieved, which allowed the complete stereochemical assign ment of aetheramides for the first time. With a longest linear sequence of 15 steps, the convergent, fully stereocontrolled route provided aetheramides A and B in 5.3% and 3.6% yields, respectively. The synthetic strategy features efficient Stille coupling for macrocyclization, asymmetric aldol reactions to establish the ambiguous stereochemistries at C-17 and C-26, and implementation of mild conditions to avoid the epimerization of the sensitive polyketide moiety and the migration of the labile lactone.

• 出版日期2016-9-16
• 单位重庆大学