141992-10-1Relevant articles and documents
High-pressure access to the Δ9-cis - And Δ9-trans-tetrahydrocannabinols family
Minuti, Lucio,Ballerini, Eleonora
, p. 5392 - 5403 (2011)
Diels-Alder reactions of a range of 1-(alkoxy/alkyl-substituted phenyl)buta-1,3-dienes with methyl vinyl ketone and methyl acrylate carried out in ethanol as the reaction medium under 9 kbar pressure were investigated. The use of high pressure as the activating method of the Diels-Alder reactions allows the efficient and endodiastereoselective generation of a series of cis-cyclohexenyl-benzene cycloadducts, which are selectively converted into their trans-epimers. The cis-cyclohexenyl-benzenes and trans-cyclohexenyl- benzenes produced are useful precursors for accessing substituted privileged cis-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene and trans-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene skeletons. The total syntheses of Δ9-cis- tetrahydrocannabinol (THC) and Δ9-trans-THC, through the use of selected Diels-Alder adducts, are described. Finally, a route for obtaining Δ9-trans-THC in both enantiomeric pure forms based on the (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP)-hydrazone method is also reported.
ALBANINS F AND G, NATURAL DIELS-ALDER ADDUCTS FROM MULBERRY
Takasugi, Mitsuo,Ishikawa, Shin-ichi,Nagao, Shigemitsu,Masamune, Tadashi,Shirata, Akira,Takahashi, Kokichi
, p. 1577 - 1580 (2007/10/02)
The structure elucidation of albanins F and G, two of the preexisting antifungal principles of shoot epidermis of mulberry, is described.