72312-15-3Relevant academic research and scientific papers
Stereoselective Total Syntheses of(+/-)-Gymnomitrol and (+/-)-Gymnomitrene
Welch, Steven C.,Chayabunjonglerd, Suthep,Rao, A.S.C.Prakasa
, p. 4086 - 4093 (1980)
Stereoselective total syntheses of (+/-)-gymnomitrol (2A) and (+/-)-gymnomitrene (2B)in 12 synthetic stages each from 2-methylcyclopentanone (3)are presented.The key features of these syntheses are (a)the conjugate addition of lithium dimethylcopper to enone 8 followed by alkylation of the intermediate enolate anion with allyl chloride to afford ketone 9, (b) stereoselective alkylation of ketone 9,(c) a modified intramolecular Claisen condensation and enolate anion trapping with tert-butyldimethylsilyl chloride to give tricyclic ketone 14B, and (d) convenient utilization of a common intermediate in the construction of both natural products 2A and 2B by sequential chemical manipulation of 15A followed by desilylation to produce either ketone 16 or 18 in one-pot reactions.
Carbonyl-Protected β-Lithio Aldehydes and Ketones via Reductive Lithiation. A General Preparative Method for Remarkably Versatile Homoenolate Equivalents
Cherkauskas, John P.,Cohen, Theodore
, p. 6 - 8 (2007/10/02)
A general procedure for producing homoenolate equivalents consists of reductive lithiation, induced by 4,4'-di-tert-butylbiphenylide, of carbonyl-protected β-(phenylthio) carbonyl compounds prepared in turn by thiophenol addition to enones or the alkylati
MICHAEL REACTION OF SILYL ENOL ETHERS OR KETENE SILYL ACETALS WITH CONJUGATED NITRO OLEFINS ACTIVATED BY THE LEWIS ACID: NEW SYNTHESIS OF 1,4-DIKETONES AND gamma -KETO ESTERS.
Miyashita,Yanami,Kumazawa,Yoshikoshi
, p. 2149 - 2156 (2007/10/02)
New one-pot procedures for the synthesis of 1,4-diketones and gamma -keto esters utilizing conjugated nitro olefins are described. Reaction of silyl enol ethers with aliphatic nitro olefins in the presence of a Lewis acid affords 1,4-diketones in good yie
