130514-62-4Relevant academic research and scientific papers
Experiments Directed Towards the Synthesis of Anthracyclinones. XX. Titanium(IV)- and Tin(IV)-Mediated Cyclizations of ortho-Allyl-Substituted Homochiral Dioxans
Cambie, Richard C.,Higgs, Kerianne C.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 1295 - 1320 (2007/10/02)
Titanium(IV) chloride mediated cyclization of the ortho-methoxylated 1,3-dioxan (5) gives a high yield of a mixture (10:1) of the (7R)-tetracycles (18) and (19) which are epimeric at C 9.The exclusive formation of the (7R) stereochemistry results from Ss
Experiments Directed Towards the Synthesis of Anthracyclinones. XV Novel Synthetic Homochiral Chloroanthracyclines from Acetal Cyclization
Brown, Edward G.,Cambie, Richard C.,Holroyd, Stephen E.,Johnson, Martin,Rutledge, Peter S.,Woodgate, Paul D.
, p. 1019 - 1034 (2007/10/02)
Quinizarin (3) has been converted in seven steps into the homochiral acetal (14) in 69 percent 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.
