cas 83729-01-5, SALVINORIN A(P) | Articles data

Articles about 83729-01-5Total 7 be found

Total Synthesis of (?)-Salvinorin A
Salvinorin A (1) is natural hallucinogen that binds the human κ-opioid receptor. A total synthesis has been developed that parlays the stereochemistry of l-(+)-tartaric acid into that of (?)-1 via an unprecedented allylic dithiane intramolecular Diels–Alder reaction to obtain the trans-decalin scaffold. Tsuji allylation set the C9 quaternary center and a late-stage stereoselective chiral ligand-assisted addition of a 3-titanium furan upon a C12 aldehyde/C17 methyl ester established the furanyl lactone moiety. The tartrate diol was finally converted into the C1,C2 keto-acetate.
Line, Nathan J.,Burns, Aaron C.,Butler, Sean C.,Casbohm, Jerry,Forsyth, Craig J.
p. 17983 - 17986
(2016)
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Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum
Transformations that selectively modify the furan ring present in a variety of naturals products would be useful in the synthesis of biological probes but remain largely underexplored. The neoclerodane diterpene salvinorin A, isolated from Salvia divinorum, is an example of a furan-containing natural product. Following selective bromination of salvinorin A, Suzuki-Miyaura and Sonogashira couplings were accomplished in moderate to good yields without hydrolyzing the labile C-2 acetate or altering the stereochemistry of the epimerizable centers.
Riley, Andrew P.,Day, Victor W.,Navarro, Hernan A.,Prisinzano, Thomas E.
p. 5936 - 5939
(2013)
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Divinorium A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint Salvia Divinorum
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Valdes, Leander J.,Butler, William M.,Hatfield, George M.,Paul, Ara G.,Koreeda, Masato
p. 4716 - 4720
(1984)
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A Protecting-Group-Free Synthesis of (?)-Salvinorin A
A concise enantioselective total synthesis of the neoclerodane diterpene (?)-salvinorin A is reported. The stereogenic center at C-12 was installed by catalytic asymmetric propargylation with excellent enantioselectivity, and the remaining six stereogenic centers were set up highly diastereoselectively under substrate control. As for our previous synthesis of racemic salvinorin A, two intramolecular Diels-Alder reactions were applied to generate the tricyclic core. A chemoselective Mitsunobu inversion of a syn 1,2-diol allowed for further streamlining of the original reaction sequence by two steps. Overall, (?)-salvinorin A was synthesized in only 16 steps starting from 3-furaldehyde with 1.4 % total yield. Furthermore, an alternative intramolecular Diels-Alder strategy employing a 2-bromo-1,3-diene moiety was investigated.
Metz, Peter,Wang, Yuzhou,Zimdars, Patrick
supporting information
p. 7968 - 7973
(2021/05/17)

Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A
(Chemical Equation Presented) Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective K-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.
Nozawa, Masato,Suka, Yuhki,Hoshi, Takashi,Suzuki, Toshio,Hagiwara, Hisahiro
supporting information; experimental part
p. 1365 - 1368
(2009/04/12)

Asymmetric synthesis of salvinorin A, a potent κ opioid receptor agonist
The stereoselective synthesis of salvinorin A is described. A macrocyclic bis-Michael reaction cascade provides the requisite tricyclic skeleton as a single diastereomer. Copyright
Scheerer, Jonathan R.,Lawrence, Jonathan F.,Wang, Grace C.,Evans, David A.
p. 8968 - 8969
(2008/02/12)

OPIOID RECEPTOR LIGANDS
The invention provides novel compounds of formula (I), (II), (III), and (IV). The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating diseases associated with opioid receptor function by administer
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Page/Page column 33-34

(2008/06/13)