Anthracyclinones. Part 2. The use of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose as a chiral template precursor in an anthracyclinone synthesis
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1279-1282
- https://doi.org/10.1039/p19840001279
Abstract
Reaction of 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdofuranose-(1,4)(7a) with leuco-quinizarin (3) in alkaline solution at 0 °C, followed by aerial oxidation, gave a good yield of (5S)-3-O-benzyl-1,2-O-isopropylidene-5-(quinizarin-2-yl)-α-D-xylofuranose (8) which with acid produced (5S)-3-O-benzyl-5-(quinizarin-2-yl)-α(β)-D-xylopyranose (11). Reaction of (11) with periodate, cold alkaline dithionite, aerial oxidation, and acid treatment gave the O-benzyl pentahydroxy anthracyclinone (13). Structures of the compounds were confirmed by u.v., mass, i.r., and 1H n.m.r. spectroscopy.This publication has 1 reference indexed in Scilit:
- Anthracyclinones. Part 1. A versatile synthesis of the anthracyclinone system using a chiral template derived from a carbohydrateJournal of the Chemical Society, Perkin Transactions 1, 1983