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83729-01-5Relevant articles and documents
Total Synthesis of (?)-Salvinorin A
Line, Nathan J.,Burns, Aaron C.,Butler, Sean C.,Casbohm, Jerry,Forsyth, Craig J.
, p. 17983 - 17986 (2016)
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.
Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum
Riley, Andrew P.,Day, Victor W.,Navarro, Hernan A.,Prisinzano, Thomas E.
, p. 5936 - 5939 (2013)
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.
A Protecting-Group-Free Synthesis of (?)-Salvinorin A
Metz, Peter,Wang, Yuzhou,Zimdars, Patrick
supporting information, p. 7968 - 7973 (2021/05/17)
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.
Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A
Nozawa, Masato,Suka, Yuhki,Hoshi, Takashi,Suzuki, Toshio,Hagiwara, Hisahiro
supporting information; experimental part, p. 1365 - 1368 (2009/04/12)
(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.
Asymmetric synthesis of salvinorin A, a potent κ opioid receptor agonist
Scheerer, Jonathan R.,Lawrence, Jonathan F.,Wang, Grace C.,Evans, David A.
, p. 8968 - 8969 (2008/02/12)
The stereoselective synthesis of salvinorin A is described. A macrocyclic bis-Michael reaction cascade provides the requisite tricyclic skeleton as a single diastereomer. Copyright
OPIOID RECEPTOR LIGANDS
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Page/Page column 33-34, (2008/06/13)
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