159247-18-4Relevant articles and documents
An efficient, stereoselective synthesis of (-)-bulgecinine from (S)-aspartic acid
Fehn, Susanna,Burger, Klaus
, p. 2001 - 2005 (1997)
A stereoselective synthesis of (2S,4S,5R)-4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)2]2 catalyzed stereospecific transformation (de >98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de >88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3.
A glycal based approach to the synthesis of (+)-bulgecinine, 3-hydroxy-2,5-dihydroxymethylpyrrolidine and 2-oxapyrrolizidin-3-one
Mishra, Umesh K.,Ramesh, Namakkal G.
, (2020)
A glycal based synthesis of (+)-bulgecinine, 3-hydroxy-2,5-dihydroxymethylpyrrolidine and 2-oxapyrrolizidin-3-ones proceeding through a common intermediate is reported. The key step in the work presented here is a two-step conversion of 4,6-di-O-benzyl-D-glucal to 2,3-dideoxy-2-tosylamido-D-glucose. This manuscript reports the first carbohydrate based approach to the synthesis of (+)-bulgecinine and the whole sequence has been accomplished with complete stereochemical integrity without the formation of mixture of products in any of these steps.
Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors
Wang, Jen-Tsung,Lin, Ting-Chien,Chen, Ying-Hsuan,Lin, Chun-Hung,Fang, Jim-Min
, p. 783 - 791 (2013/08/26)
Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2-4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases. The Royal Society of Chemistry 2013.
An asymmetric dihydroxylation route to (-)-bulgecinine
Show, Krishanu,Upadhyay, Puspesh K.,Kumar, Pradeep
, p. 1234 - 1238 (2011/10/19)
The stereoselective synthesis of (-)-bulgecinine is reported from L-aspartic acid using Sharpless asymmetric dihydroxylation and intramolecular cyclization via nucleophilic displacement of a-tosylate as key steps.
Palladium-catalyzed DYKAT of butadiene monoepoxide: Enantioselective total synthesis of (+)-DMDP, (-)-bulgecinine, and (+)-broussonetine G
Trost, Barry M.,Horne, Daniel B.,Woltering, Michael J.
, p. 6607 - 6620 (2008/09/16)
Palladium catalyzed asymmetric allylic alkylation reaction of an amine with two equivalents of butadiene monoxide allows for the expedient synthesis of trans- and cis-2,5-dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of iminosugar natural products was demonstrated with the short and high yielding asymmetric syntheses of (+)-DMDP, and (-)-bulgecinine. In addition, the first total synthesis of (+)-broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration.
An efficient stereoselective synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine
Chavan, Subhash P.,Praveen, Cherukupally,Sharma, Pallavi,Kalkote
, p. 439 - 441 (2007/10/03)
A short synthetic route to (-)-and (+)-bulgecinine, the amino acid moiety of the bulgecins was achieved from the readily available nonchiral pool starting material cis-2-butene-1,4-diol employing a Claisen orthoester rearrangement and Sharpless asymmetric
An efficient stereoselective synthesis of (2S,4S,5R)-(-)-bulgecinine
Krasiński, Antoni,Jurczak, Janusz
, p. 2019 - 2021 (2007/10/03)
N-Benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-d-serinal (6) was reacted under Barbier conditions with allyl bromide affording diastereoselectively (82:18) the anti-adduct 5, which was subsequently transformed into (2S,4S,5R)-(-)-bulgecinine (1).
Total synthesis of (-)-bulgecinine
Maeda, Mikiko,Okazaki, Fumiaki,Murayama, Mayumi,Tachibana, Yohko,Aoyagi, Yutaka,Ohta, Akihiro
, p. 962 - 965 (2007/10/03)
A short synthetic route to (-)-bulgecinine (1), the amino acid moiety of bulgecins, was established by using 1,3-dipolar cycloaddition of N-benzyl- α-methoxycarbonylmethanimine N-oxide (6) to a chiral allylic alcohol (5) with moderate threo selectivity as the key reaction.
An improved procedure for the enantioselective synthesis of (+)- and (-)-cis-4-hydroxyprolines and bulgecinines
Graziani, Lucia,Porzi, Gianni,Sandri, Sergio
, p. 1341 - 1346 (2007/10/03)
An efficient enantioselective synthesis of both the enantiomers of cis-4-hydroxy-proline and bulgecinine was accomplished starting from synthons 1 or 1'. The improved synthetic route to the aforesaid enantiomerically pure proline derivatives was established via a stereocontrolled double iodocyclization of 3(a,b) or 3'(a,b).
Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (-)-desoxoprosopinine
Yuasa, Yoko,Ando, Jun,Shibuya, Shiroshi
, p. 793 - 802 (2007/10/03)
Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.
