
TY  - JOUR
A1  - Brown, EG 
A1  - Cambie, RC 
A1  - Holroyd, SE 
A1  - Johnson, M 
A1  - Rutledge, PS 
A1  - Woodgate, PD 
T1  - Experiments Directed Towards the Synthesis of Anthracyclinones. XV. Novel Synthetic Homochiral Chloroanthracyclines From Acetal Cyclization
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 6
SP  - 1019
EP  - 1034
KW  - 
UR  - https://doi.org/10.1071/CH9901019 
N2  - 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. 
ER  -

