STEREOSELECTIVE TOTAL SYNTHESES OF (-)-DESOXOPROSOPININE AND (-)-DESOXOPROSOPHYLLINE - PALLADIUM(0)-CATALYZED INTRAMOLECULAR N-ALKYLATION FOR THE KEY PIPERIDINE RING FORMATION

Authors
TAKAO K NIGAWARA Y NISHINO E TAKAGI I MAEDA K TADANO K OGAWA S
Citation
K. Takao et al., STEREOSELECTIVE TOTAL SYNTHESES OF (-)-DESOXOPROSOPININE AND (-)-DESOXOPROSOPHYLLINE - PALLADIUM(0)-CATALYZED INTRAMOLECULAR N-ALKYLATION FOR THE KEY PIPERIDINE RING FORMATION, Tetrahedron, 50(19), 1994, pp. 5681-5704
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
19
Year of publication
1994
Pages
5681 - 5704
Database
ISI
SICI code
0040-4020(1994)50:19<5681:STSO(A>2.0.ZU;2-T
Abstract
Intramolecular N-alkylation of D-glucose-derived substrate 21E proceed ed in an S(N)2' mode smoothly in the presence of a Pd(O) catalyst and n-Bu(4)NI. The major cyclization product, a 2,6-dialkylated piperidine 22t, was effectively converted into the title alkaloids.