Experiments Directed Towards the Synthesis of Anthracyclinones .XIV. An Intermediate for the Synthesis of Vineomycins

Abstract

Anthrarufin (4) has been converted by a high-yielding route involving sequential reductive Claisen rearrangements into 1-acetoxy-5-methoxy-9,10-dioxo-6-(2'-oxopropy1)-9,10-dihydroanthracene-2-carbaldehyde (3), an intermediate which is suitable for the synthesis of vineomycins . The thermal Claisen rearrangements of some allyl ethers of 1,5-dihydroxyanthraquinone have been examined.