Synthesis of (L)-daunosamine and related amino sugars
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 111-123
- https://doi.org/10.1039/p19880000111
Abstract
1-(2-Furyl)ethanol (6) has been converted into methyl (±)-daunosaminide (1) and methyl (±)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (±)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate. Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.This publication has 8 references indexed in Scilit:
- Stereoselective syntheses of (.+-.)-daunosamine, (.+-.)-vancosamine, and (.+-.)-ristosamine from acyclic precursorsThe Journal of Organic Chemistry, 1986
- A new approach to the synthesis of hexoses: an entry to (.+-.)-fucose and (.+-.)-daunosamineJournal of the American Chemical Society, 1985
- Total synthesis of acosamine and daunosamine utilizing a diastereoselective intramolecular [3+2] cycloadditionTetrahedron, 1985
- Regio- and stereoselective synthesis of methyl .alpha.-L-daunosaminide hydrochlorideThe Journal of Organic Chemistry, 1984
- Stereoselection in acyclic systems. The synthesis of amino sugars via nitrone cycloadditionsJournal of the American Chemical Society, 1984
- Synthesis of daunosamineThe Journal of Organic Chemistry, 1983
- Synthesis of (+)-cis-1-methoxy-4.beta.-carbomethoxy-4a,5,8,8a-tetrahydroisochroman, a synthon for the preparation of alkaloids and iridoidsThe Journal of Organic Chemistry, 1979
- Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease.Clinical evaluation with special reference to childhood leukemiaCancer, 1967