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

Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides.
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Qi N, Allu SR, Wang Z, Liu Q, Guo J, He Y,


Qi N, Allu SR, Wang Z, Liu Q, Guo J, He Y, (click to view)

Qi N, Allu SR, Wang Z, Liu Q, Guo J, He Y,

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Organic letters 2016 09 0718(18) 4718-21 doi 10.1021/acs.orglett.6b02371

Abstract

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 assignment 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.

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