
%0 Journal Article
%A Brown, EG 
%A Cambie, RC 
%A Holroyd, SE 
%A Johnson, M 
%A Rutledge, PS 
%A Woodgate, PD 
%T Experiments Directed Towards the Synthesis of Anthracyclinones. XV. Novel Synthetic Homochiral Chloroanthracyclines From Acetal Cyclization
%J Australian Journal of Chemistry
%D 1990/06/01
%V 43
%N 6
%P 1019-1034
%K 
%R https://doi.org/10.1071/CH9901019
%U https://www.publish.csiro.au/paper/CH9901019 
%X Quinizarin (3) has been converted in seven steps into the homochiral acetal (14) in 69% overall yield, through a sequence involving reductive Claisen rearrangements of the allyl ethers (8) and (20). The acetal (15) has been converted into four novel diastereomeric 9-chloroanthracyclines (31)-(34) by an unprecedented intramolecular acetal-alkene cyclization mediated by tin(IV) chloride in N,N-dimethylformamide. 
