Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (–)-desoxoprosopinine
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 793-802
- https://doi.org/10.1039/p19960000793
Abstract
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.Keywords
This publication has 24 references indexed in Scilit:
- Highly diastereoselective route to trans-5-substituted 2-hydroxymethylpyrrolidine derivatives by radical cyclisationJournal of the Chemical Society, Perkin Transactions 1, 1996
- Enantioselective Synthesis of (−)-desoxoprosopinine by radical cyclizationTetrahedron: Asymmetry, 1995
- A new route to chiral pyrrolidines via radical cyclisation; enantioselective synthesis of (+)-bulgecinineJournal of the Chemical Society, Chemical Communications, 1994
- A new enantioselective synthesis of trans 2,5-disubstituted pyrrolidine derivatives by radical cyclisationJournal of the Chemical Society, Chemical Communications, 1994
- Short, stereoselective syntheses of 4,5,6-trihydroxylated norleucines: An approach to the synthesis of (+)-bulgecinineTetrahedron Letters, 1993
- Tributyltin hydride-induced O-stannyl ketyls in the cyclization of aldehydes and ketones with alkenesTetrahedron Letters, 1989
- Stereoselective hydroxylation of N-carbamoyl-L-pyroglutamate. Synthesis of (−)-bulgecinineTetrahedron Letters, 1988
- A novel stereospecific radical cyclization of 2′,3′-O-isopropylideneuridine and -adenosine 5′-aldehyde to the corresponding 6,5′-cyclodihydrouridine and 8,5′-cycloadenosine derivativesTetrahedron Letters, 1988
- Synthesis of 2s, 4s, 5s -dihydroxypipecolic acid and bulgecinine [2s,4s,5r-4-hydroxy-5- (hydroxymethyl)proline] from d-glucuronolactone, a strategy for the synthesis of 2s,4s-4-hydroxy-α-amino acidsTetrahedron, 1987
- Structures of bulgecins, bacterial metabolites with bulge-inducing activityTetrahedron, 1984