20036-53-7Relevant academic research and scientific papers
A Concise Total Synthesis of (±)-Mesembrine
Kim, Hyoungsu,Choi, Hosam,Lee, Kiyoun
, p. 1203 - 1206 (2018/02/26)
A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson-Claisen rearra
Concise Total Syntheses of (±)-Joubertiamine, (±)- O -Methyljoubertiamine, (±)-3′-Methoxy-4′- O -methyljoubertiamine, (±)-Mesembrane, and (±)-Crinane
Das, Mrinal Kanti,De, Subhadip,Bisai, Alakesh
, p. 2093 - 2104 (2016/07/06)
A method to access cis-3a-aryloctahydroindole alkaloids has been developed through a key strategy involving Eschenmoser-Claisen rearrangement of allylalcohol. This approach gives us an opportunity to access the all-carbon quaternary center required for ci
Concise total syntheses of (±)-mesembrane and (±)-crinane
Das, Mrinal Kanti,De, Subhadip,Shubhashish,Bisai, Alakesh
supporting information, p. 3585 - 3588 (2015/03/30)
A straightforward and unified strategy to access Amaryllidaceae alkaloids comprising a cis-3a-aryloctahydroindole scaffold has been developed. The strategy features Eschenmoser-Claisen rearrangement of allylalcohol as a key step for the installation of al
A New Approach to Morphinans: Total Synthesis of O-Methylpallidinine
McMurry, John E.,Farina, Vittorio,Scott, William J.,Davidson, Alan H.,Summers, David R.,Shenvi, Ashok
, p. 3803 - 3812 (2007/10/02)
We have devised a general method for the synthesis of 4a-aryloctahydroisoquinolines related to morphine and have shown how these compounds may be used in a route to morphinan alkaloids.The key step in this route involves the addition of diazomethane to a 4a-aryloctahydroisoquinolinium salt, followed by spontaneous cyclization to the morphinan.Studies of this step indicate that it is not compatible with the presence of an alkoxyl group at C4 of the aryl ring.The value of this method has been demonstrated in the context of stereospecific total synthesis of O-methylpallidinine.
Alkaloid Synthesis via Intramolecular Ene Reaction. 2. Application to dl-Mesembrine and dl-Dihydromaritidine
Keck, Gary E.,Webb, Robert R.
, p. 1302 - 1309 (2007/10/02)
The total syntheses of mesembrine (2) and dihydromaritidine (3), alkaloids of the genera Sceletium and Amaryllis (respectively), are decscribed.The key strategy in each case involves the intramolecular ene cyclization of an appropriately constructed acylnitroso olefin, giving cyclic hydroxamic acid ("ene product") 12.Reduction of the hydroxamic acid to the lactam 4 is followed by N-methylation and hydroxylation at position C-6 via bromohydrin 15, introducing the oxygen functionality present in 2.Removal of bromine, oxidation of the alcohol to the keto lactam 13, andreductive removal of the lactam carbonyl gave racemic mesembrine.Removal of bromine from bromohydrin 20, obtained from lactam 4, followed by reduction with lithium aluminum hydride and Pictet-Spengler cyclization gave dihydromaritidine (3).
