Stereoselective synthesis of marine macrolide Aspergillide D

Abstract

A formal stereoselective synthesis of the naturally occurring 16-membered macrolide aspergillide D is described. The origins of the chiral centers are ribose, lactic acid and the Sharpless asymmetric epoxidation protocol. The foremost reactions involved are Yadav's protocol, the Ohira-Bestmann reaction and alkyl-iodide coupling.

Asymmetric total synthesis of antiviral agents (+)-sattazolin and (+)-sattabacin

“…This protected compound 7 was used as common intermediate for both the target compounds. It has already been reported 4 that the direct opening of epoxy ketone 6 with indole in presence of Lewis acid (Yb(OTf)3) did not allow to furnish compound 1. To overcome this we have protected the epoxy ketone as dimethylacetal 7.…”

“…Miller et al reported the first asymmetric total synthesis of the sattabacin and sattazolin in three and seven overall steps respectively. 3,4 Their structural similarity, no complexity and interesting biological activity of both the natural products drove us to their total synthesis.…”

“…As part of our regular research program on the synthesis of biologically active natural and synthetic compounds, [5][6][7][8][9] we herein report the total synthesis of antiviral agents of (+)-sattazolin and (+)-sattabacin (Figure -1).…”