87900-51-4Relevant articles and documents
Gossypium Cadinanes and Their Analogues: Synthesis of Lacinilene C, 2,7-Dihydroxycadalene, and Their Methyl Ethers
McCormick, John P.,Shinmyozu, Teruo,Pachlatko, J. Paul,Schafer, Tann R.,Gardner, Jeffrey W.,Stipanovic, Robert D.
, p. 34 - 40 (1984)
The total synthesis of lacinilene C methyl ether has been accomplished in ten steps with an overall, optimal yield of 38percent by starting with o-methylanisole.Formation of the key α-aryl-α-ketol functionality, which is particularly sensitive to oxidation, was accomplished by stepwise oxidation reactions based on the use of N-methylmorpholine N-oxide/osmium tetraoxide acting on alkene and trimethylsilyl enol ether functionality.Other oxidations could be accomplished by using dichlorodicyanobenzoquinone to generate unsaturation adjacent to the α-ketol group or to form substituted naphtalenes.These reactions permitted adjustment of the oxidation level and oxygenation pattern of the key intermediate, 7-methoxy-α-calacorene (3,4-dihydro-4-isopropyl-7-methoxy-1,6-dimethylnaphthalene), to accomplish the synthesis of 2-hydroxy-7-methoxycadalene, 2,7-dihydroxycadalene, 7-methoxycadalene, and 7-hydroxycadalene, in addition to lacinilene C and its methyl ether.