Literature DB >> 30405274

Stereoselective Synthesis of 5-O-Carbamoylpolyoxamic Acid by [2,3]-Wittig-Still Rearrangement.

Arun K Ghosh1, Yong Wang1.   

Abstract

Stereoselective [2,3]-Wittig rearrangement of E- and Z-allylic stannyl ethers derived from an isopropylidene L-threitol derivative has been investigated. The E-isomer exhibited best diastereoselectivity and the resulting rearrangement product has been converted to protected polyoxamic acid, an amino acid component of many bioactive polyoxins.

Entities:  

Keywords:  amino acids and derivatives; carbamates rearrangement; stereoselection; tin and compounds

Year:  2000        PMID： 30405274      PMCID： PMC6217795          DOI： 10.1016/S0040-4020(99)00838-8

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  3 in total

1.  Theory and modeling of stereoselective organic reactions.

Authors:  K N Houk; M N Paddon-Row; N G Rondan; Y D Wu; F K Brown; D C Spellmeyer; J T Metz; Y Li; R J Loncharich
Journal:  Science       Date:  1986-03-07       Impact factor: 47.728

2.  Transition-State Mimetics for HIV Protease Inhibitors: Stereocontrolled Synthesis of Hydroxyethylene and Hydroxyethylamine Isosteres by Ester-Derived Titanium Enolate Syn and Anti-Aldol Reactions.

Authors:  Arun K. Ghosh; Steve Fidanze
Journal:  J Org Chem       Date:  1998-09-04       Impact factor: 4.354

3.  Stereoselective Synthesis of Protected Thymine Polyoxin C via [2,3]-Wittig-Still Rearrangement of Ribose-Derived Allylic Stannyl Ethers.

Authors:  Arun K Ghosh; Yong Wang
Journal:  J Org Chem       Date:  1998-08-29       Impact factor: 4.354
  3 in total

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