A new synthetic approach towards adriamycin
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 643-647
- https://doi.org/10.1039/p19800000643
Abstract
An improved route to 3,4-dihydro-2-phenylnaphtho[1,8-b,c]furan-5-one (2) and a convenient preparation of furan-3,4-dicarbaldehyde (4) are described. The dihydro-derivative of (2) was condensed with (4) to give 4-(4-formyl-3-furylmethyl)-2-phenylnaphtho[1,8-b,c]furan-5-one (5), which after preparation of its 1,3 dithiolan derivative was photocyclised to a polycyclic compound (7). Owing to problems of deprotection of (7) further steps towards adriamycin (1) were abandoned.This publication has 3 references indexed in Scilit:
- Stereoselektive Totalsynthese von AnthracyclinonenEuropean Journal of Inorganic Chemistry, 1978
- 4a,9a-Epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetrone: a versatile synthon in anthracyclinone synthesisJournal of the Chemical Society, Chemical Communications, 1978
- Synthetic approaches to adriamycin. 2. Degradation of daunorubicin to a nonasymmetric tetracyclic ketone and refunctionalization of the A ring to adriamycinThe Journal of Organic Chemistry, 1977