74807-65-1Relevant academic research and scientific papers
THE BIOSYNTHESIS OF QUADRONE AND TERRECYCLIC ACID
Cane, David E.,Whittle, Yvonne G.,Liang, Tzyy-Chyau
, p. 1119 - 1122 (1984)
Feedings of - and acetate to Aspergillus terreus gave quadrone and terrecyclic acid which were analyzed by 13C NMR.The pattern of 13C-enrichments and couplings is consistent with the formation of 1 and 2 by cyclization of farnesyl pyrophosphate.
The Total Synthesis of dl-Quadrone
Danishefsky, Samuel,Vaughan, Kenward,Gadwood, Robert,Tsuzuki, Kazuo
, p. 4136 - 4141 (2007/10/02)
A regio- and stereospecific total synthesis of dl-quadrone (1) is described.The synthesis, which starts with 4,4-dimethylcyclopent-2-en-1-one (5), is accomplished in 19 steps in 3.1percent yield.The key intermediates are the enone ester 4, the iodo ketal 15, the tricyclic keto ester 16, and the hydroxymethyl keto acid 22.The latter as well as the seco acid 2 afford quadrone upon thermolysis.
