116324-55-1Relevant articles and documents
Synthetic Anthracyclinones, 36. - Convergent Synthesis of Enantiomerically Pure Daunomycinone Derivatives
Krohn, Karsten,Rieger, Hagen,Broser, Erwin,Schiess, Peter,Chen, Shizhi,Strubin, Thomas
, p. 943 - 948 (2007/10/02)
The ortho-quinoid vinylketenes 12 and 13 can be generated thermally or photochemically from the benzocyclobutenones 3 and 4.They undergo cycloaddition with the substituted benzoquinone 14 to yield the isomeric tetracyclic compounds 15, 16, 19, and 20 which can be oxidized to give the 10-deoxydaunomycinone derivatives 23 and 24.A similar cycloaddition of bisketenes obtained photolytically from the corresponding benzocyclobutenediones 9-11 with the enantiomerically pure AB building block 29 affords the symmetrically substituted daunomycinones 33-35 in only two steps.
