Diastereoselective and convergent synthesis of both 11′-epimers of (-)-(2R,3R,6S)-carnavaline

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7255-7266

  Pahl, Axel ^a   Oetting, Jörg ^a   Holzkamp, Jens ^a   Meyer, Hartmut H ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARNAVALINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030979195     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00428-6     Document Type: Article

References (17)

1. (a) Lythgoe, D.; Vernengo, M.J.; Tetrahedron Lett. 1967, 1133.
2. (b) Bolzani, V.d.S.; Gunatilaka, A.A.L.; Kingston, D.G.I.; Tetrahedron 1995, 51(21), 5929.
3. (a) Strunz, G.M.; Findlay, J. A. in: The Alkaloids, Brossi, A., Ed; Academic Press: New York 1985; Vol.26, 89.
4. (b) Wang, C.-L.J.; Wuonola, M.A.; Org. Prep. Proc. Int. 1992, 24, 585.
5. (c) Pinder, A.R.; Nat. Prod. Rep. 1992, 9, 17.
6. (d) Pinder, A.R.; Nat. Prod. Rep. 1992, 9, 491.
7. 3 and chiral 1,2-aminoalcohols see e.g.: Corey, E.J., Bakshi, R.K; Shibata, S.; J. Am. Chem. Soc. 1987, 109, 5551.
8. Meyer, H.H.; Holzkamp, J.; Oetting, J.; Pahl, A.; Tetrahedron Asymm. 1997, 8(3), 477.
9. No sign of decomposition appeared after storage for 1 year under nitrogen at -16°C.
10. Camps, F.; Casamor, J.M.; Coll, J.; Guerrero, A.; Riba, M.; Org. Prep. Proc. Int. 1983, 15(1-2), 63.
11. (S)- and (R)-propylene oxide were purchased from Fluka.
12. Quinkert, G.; Fernholz, E.; Eckes, P.; Neumann, D.; Dürner, G.; Helv. Chim. Acta 1989, 72, 1753.
13. 3 of the acetates of 15, and was determined to be higher than 98% ee.
14. Due to the risk resulting from the possible presence of peroxides.
15. Quinkert, G.; Billhardt, U.-M.; Jakob, H.; Fischer, G.; Glenneberg, J.; Nagler, P.; Autze, V.; Heim, N.; Wacker, M.; Schwalbe, T.; Kurth, Y.; Bats, J.W.; Dürner, G.; Zimmermann, G.; Kessler, H.; Helv. Chim. Acta 1987, 70, 771.
16. Cook, W.; Miller, R.G.J.; Todd, P.F.; J. Organomet. Chem. 1969, 19, 421.
17. Baldwin, J.E; Adlington, R.M; Ramcharitar, S.H.; Tetrahedron 1992, 48(16), 3413.