Synthesis of Orthogonally Protected (2R,3R,4S)-4-Amino-2,3-dihydroxyheptane-1,7-dioic Acid

Abstract (2 R ,3 R ,4 S )-4-Amino-2,3-dihydroxyheptane-1,7-dioic acid, a common component of cyclic depsipeptide homophymines with anti-HIV activity, was synthesized as its orthogonally protected derivative from Fmoc-Glu( t -Bu)-OH in 6 steps. Osmium-catalyzed dihydroxylation of γ-amino- Z -α,β-unsa...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2014-11, Vol.47 (3), p.351-358
Main Authors: Tokairin, Yoshinori, Maita, Kakeru, Takeda, Sho, Konno, Hiroyuki
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract (2 R ,3 R ,4 S )-4-Amino-2,3-dihydroxyheptane-1,7-dioic acid, a common component of cyclic depsipeptide homophymines with anti-HIV activity, was synthesized as its orthogonally protected derivative from Fmoc-Glu( t -Bu)-OH in 6 steps. Osmium-catalyzed dihydroxylation of γ-amino- Z -α,β-unsaturated esters gave the dihydroxy esters with moderate diastereoselectivity. The stereochemistries of the amino acids­ were determined by comparison of 1 H NMR spectra.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378902