The Journal of organic chemistry

Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure

WR Roush, RJ Neitz

Index: Roush, William R.; Neitz, R. Jeffrey Journal of Organic Chemistry, 2004 , vol. 69, # 15 p. 4906 - 4912

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Citation Number: 32

Abstract

The originally proposed structure (2) of landomycinone, the aglycone of landomycin A, has been synthesized and shown to be nonidentical to the naturally derived landomycin A aglycone. The synthesis of 2 features the Dötz benzannulation reaction of chromium carbene 5 and alkyne 6, and the intramolecular Michael-type cyclization reaction of the phenolic naphthoquinone 20. It is proposed that natural landomycinone possesses the ...