121822-42-2Relevant academic research and scientific papers
Alkaloids of Ocotea acutangula
Vecchietti, Vittorio,Casagrande, Cesare,Ferrari, Giorgio,Danieli, Bruno,Palmisano, Giovanni
, p. 578 - 581 (1981)
The leaves of Ocotea acutangula (Mez) contain, in addition to the known (S)-(-)-pallidine (5) and its new derivative (S)-(-)-O-methylpallidine (6), the new 8,14-dihydromorphinandienone alkaloids (S)-(-)-pallidinine (7) and (S)-(-)-O-methylpallidinine (8) which possess a B/C trans-junction.
Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling
Lipp, Alexander,Selt, Maximilian,Ferenc, Dorota,Schollmeyer, Dieter,Waldvogel, Siegfried R.,Opatz, Till
, p. 1828 - 1831 (2019)
A fully regio- and diastereoselective electrochemical 4a-2′-coupling of a 3′,4′,5′-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (-)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.
The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid
Hamamoto, Hiromi,Shiozaki, Yukiko,Nambu, Hisanori,Hata, Kayoko,Tohma, Hirofumi,Kita, Yasuyuki
, p. 4977 - 4982 (2007/10/03)
The non-phenolic coupling reaction of benzyltetrahydroisoquinolines (laudanosine derivatives) by using a hypervalent iodine(III) reagent is described. In general, chemical oxidation of laudanosine gives glaucine. In contrast to general chemical oxidizing reagent systems, the novel use of reagent combination of phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) afforded morphinandienone alkaloids in excellent yields. In order to achieve the coupling reaction with simple reaction procedure, the use of HPA supported on silica gel instead of HPA was demonstrated and sufficient yield was exerted again. The present reagent system, PIFA/HPA, was also applied to the oxidation of other non-phenolic benzyltetrahydroisoquinolines and the high yield conversion to morphinandienones was accomplished.
Synthesis of optically active aporphine and morphinandienone alkaloids via p-quinol esters
Hara,Komoriya,Miyashita,Hoshino
, p. 1683 - 1692 (2007/10/02)
Lead tetraacetate oxidation of N-trifluoroacetylnorcodamine (5) in (S)-(+)-2-phenylpropionic acid gave a diastereomeric mixture of two p-quinol acylates, which were easily separated to enantiomerically pure 6a and 6b. Treatment of the chiral quinol acylates (6a) and (6b) with trifluoroacetic acid in CH2Cl2 at room temperature afforded (1R)-(-)-6-trifluoroacetylwilsonirine (7a) and (1S)-(+)-(7b), respectively. Saponification of 7a and 7b gave rise to (-)-wilsonirine (8a) and its enantiomer (8b), respectively. Similarly, (-)-nordomesticine (12a) and (+)-(12b) were synthesized in enantiomerically pure form from 10a and 10b. On the other hand, acid treatment of 6a and 6b in CH3CN at lower temperature (-30°C) llowed by N-deprotection gave the corresponding normorphinandienones (15a and 15b) as major products, which were transformed to enantiomerically pure (-)-16a and (+)-sebiferine (16b). In a similar sequence of reactions, (+)-amurine (19a) and its enantiomer (19b) were synthesized.
Electrochemical Oxidation of Morphinandienones
Christensen, Leif,Miller, Larry L.
, p. 4876 - 4880 (2007/10/02)
The (+/-)-morphinandienones, O-methylflavinantine, O-benzyllaudanine, and O-methylflavinine, were synthesized by electrochemical oxidation of laudanosine, O-benzylpalladine, and norlaudanosine.With use of acetonitrile containing fluoroboric acid as solven
