436806-94-9Relevant articles and documents
Stereoselective construction of 2,6- cis -disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: Total synthesis of (-)-centrolobine
Latif, Muhammad,Yun, Jeong In,Seshadri, Kalapati,Kim, Hyoung Rae,Park, Chi Hoon,Park, Haeil,Kim, Hyoungsu,Lee, Jongkook
, p. 3315 - 3320 (2015/03/30)
A highly stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans was achieved by using an intramolecular amide enolate alkylation with KHMDS. The efficiency and practicality of this methodology was successfully demonstrated in the total syn
Stereoselective synthesis of tetrahydropyranyl diarylheptanoids (-)-centrolobine and (+)-centrolobine
Reddy, Chada Raji,Madhavi, Pasupulety Phani,Chandrasekhar, Srivari
experimental part, p. 123 - 126 (2011/02/26)
A versatile chiron approach to the tetrahydropyranyl diarylheptanoid natural products (-)-centrolobine and (+)-centrolobine has been described. The use of an aldol reaction followed by reductive etherification for the formation of tetrahydropyran ring is of importance. Georg Thieme Verlag Stuttgart · New York.
Stereoselective formal total synthesis of novel antibiotic (-)-centrolobine
Mohapatra, Debendra K.,Pal, Rita,Rahaman, Hasibur,Gurjar, Mukund K.
experimental part, p. 219 - 227 (2010/05/03)
A concise and stereoselective formal total synthesis of (-)-centrolobine is achieved utilizing Mioskowski's Lewis acid mediated epoxide opening followed by ring-closing metathesis as the key reaction.
Stereoselective formal synthesis of (-)-centrolobine
Prasad, Kavirayani R.,Anbarasan, Pazhamalai
, p. 1089 - 1092 (2007/10/03)
Stereoselective formal synthesis of (-)-centrolobine was achieved from naturally occurring l-(+)-tartaric acid, employing a facile FeCl3 mediated stereoselective formation of a tetrahydropyran as the key step.
Reductive cyclizations of hydroxysulfinyl ketones: Enantioselective access to tetrahydropyran and tetrahydrofuran derivatives
Carreno, M. Carmen,Des Mazery, Renaud,Urbano, Antonio,Colobert, Francoise,Solladie, Guy
, p. 7779 - 7787 (2007/10/03)
The stereocontrolled formation of cis-2,5-disubstituted tetrahydrofurans and cis-2,6-disubstituted tetrahydropyrans is achieved from enantiopure ketosulfinyl esters by reduction, Weinreb's amide, and ketone formation, followed by the reductive cyclization (Et3SiH/TMSOTf) of the resulting hydroxysulfinyl ketones. The sulfoxide-bearing heterocycles were transformed into two natural products, (-)-centrolobine (1) and both enantiomers of cis-(6-methyltetrahydropyran-2-yl)acetic acid (2).
First enantioselective total synthesis of (-)-Centrolobine.
Colobert, Francoise,Mazery, Renaud Des,Solladie, Guy,Carreno, M Carmen
, p. 1723 - 1725 (2007/10/03)
[structure: see text] The first enantioselective total synthesis of (-)-Centrolobine is described. The key reaction is the synthesis of the cis-disubstituted tetrahydropyran framework by intramolecular cyclization of the enantiopure hydroxyketone 3 with E