153381-08-9Relevant articles and documents
Phlenumdines A?C, New lycopodium alkaloids isolated from phlegmariurus nummulariifolius
Nakayama, Waka,Monthakantirat, Orawan,Fujikawa, Kazumi,Watthana, Santi,Kitanaka, Susumu,Makino, Toshiaki,Ishiuchi, Kanichiro
, p. 2247 - 2261 (2017)
Three new lycopodine-type alkaloids, phlenumdines A?C (1?3), have been isolated from the clubmoss Phlegmariurus nummulariifolius (Blume) Ching, and their structures were elucidated on the basis of spectroscopic data.
Asymmetric transfer hydrogenation of α-azido acrylates
Ji, Yang,Xue, Ping,Ma, Dan-Dan,Li, Xue-Qiang,Gu, Peiming,Li, Rui
supporting information, p. 192 - 194 (2015/02/05)
The asymmetric transfer hydrogenation of α-azido acrylates has been explored, a range of α-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A.
Total synthesis of (+)-pentamethylsalvianolic acid C
Alford, Benjamin L.,Huegel, Helmut M.
supporting information, p. 2724 - 2727 (2013/06/04)
The total synthesis of a methylated analogue of (+)-Salvianolic acid C has been achieved. Key aspects of the synthetic route include an economical Cu(i) acetylide coupling, unique carboxyl activation conditions via microwave irradiation and a novel lipase catalysed kinetic resolution of a racemic mixture of secondary alcohol Danshensu. The preparation of this methylated analogue will not only improve the bioavailability, but also enable access to new and wider bioactivity applications for (+)-Salvianolic acid C.
Tricyclic CNS active agents by intramolecular Oxa-Pictet-Spengler reaction
Wunsch,Zott,Hofner,Bauschke
, p. 487 - 495 (2007/10/02)
Mitsunobu inversion of the (S)-configurated lactate (S)-7, which is prepared in four steps starting from (S)-tyrosine, leads to the (R)-configurated lactate (R)-7. The key step in the transformation of the enantiomeric lactates (S)-7 and (R)-7 into the benzomorphan analogous tricycles (R,S)-16a,b, (S,R)-16a,b, (S,S)-22, and (R,R)-22 is an intramolecular Oxa-Rictet-Spengler reaction: The amides (S)-13, (R)-13, (S)-19 and (R)-19, in which the carbonyl moiety - masked as an acetal - is linked to the 2-phenylethanol moiety, are cyclized to give the tricyclic amides (R,S)-15, (S,R)-15, (S,S)-21, and (R,R)-21, respectively. In a concentration of 100 μM both enantiomers of 16a, 16b, and 22 are not able to compete with 3H-(+)-MK 801 for the phencyclidine binding sites of NMDA receptors. In vivo, only (R,S)-16b and (S,S)-22 exhibit weak sedative and analgesic activity.
Tricyclic benzomorphan analogues by intramolecular Oxa-Pictet-Spengler reaction
Wunsch,Zott
, p. 2307 - 2310 (2007/10/02)
The key step in the regio- and stereoselective preparation of the benzomorphan analogues 9, 10a, 10b, 14 and 15 is an intramolecular Oxa-Pictet-Spengler reaction. Masked as an acetal the carbonyl component is connected via an amide to the 2-phenylethanol component (7, 12).