An efficient and stereoselective construction of the core structure of the manzamines via an intramolecular Michael reaction

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1677-1680

  Brands, K M J ^a   DiMichele, L M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; MANZAMINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BIOGENESIS; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032568228     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00019-7     Document Type: Article

References (21)

1. 1. (a) Harrison, B.; Talapatra, S.; Lobkowsky, E.; Clardy, J.; Crews, P. Tetrahedron Lett., 1996, 37, 9151-9154 and references cited therein.
2. (b) Edrada, R.A.; Proksch, P.; Wray, V.; Witte, L.; Müller, W.E.G.; Van Soest, R.W.M. J. Nat. Prod., 1996, 59, 1056-1060 and references cited therein.
3. c) Tsuda, M.; Inaba, K.; Kawasaki, N.; Honma, K.; Kobayashi, J. Tetrahedron, 1996, 52, 2319-2324 and references cited therein.
4. 2. Baldwin, J.E.; Bischoff, L.; Claridge, T.D.W.; Heupel, F.A.; Spring, D.R.; Whitehead, R.C. Tetrahedron, 1997, 53, 2271-2290 and references cited therein.
5. 3. (a) Magnier, E.; Langlois, Y.; Mérienne, C. Tetrahedron Lett., 1995, 36, 9475-9478 and reference cited therein.
6. (b) Li, S.; Ohba, S.; Kosemura, S.; Yamamura, S. Tetrahedron Lett., 1996, 37, 7365-7368 and references cited therein.
7. 4. For a recent review on intramolecular Michael reactions: Little, R.D.; Masjedizadeh, M.R.; Wallquist, O.; McLoughlin, J.I. in Organic Reactions; Paquette, L.A. (Ed.); Wiley: New York, 1995, 315-553.
8. 5. (a) Baldwin, J.E.; Miranda, T.; Moloney, M. Tetrahedron, 1989, 45, 7459-7468.
9. (b) Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Escribano, A.; Sánchez-Ferrando, F. Tetrahedron, 1993, 49, 8665-3678.
10. (c) Ezquerra, J.; Pedregal, C.; Rubio, A.; Vaquero, J.J.; Matiá, M.P.; Martín, J.; Diaz, A.; García Navío, J.L.G.; Deeter, J.B. J. Org. Chem., 1994, 59, 4327-4331.
11. (d) Ezquerra, J.; Pedregal, C.; Yruretagoyena, B.; Rubio, A.; Carreno, M.C.; Escribano, A.; García Ruano, J.L. J. Org. Chem., 1995, 60, 2925-2930.
12. (e) Dikshit, D.K.; Bajpai, S.N. Tetrahedron Lett., 1995, 36, 3231-3232.
13. 6. Ley, S.V.; Woodward, P.R. Tetrahedron Lett., 1987, 28, 3019-3020.
14. 1H-NMR compound 6 is a 4/1 mixture of trans and cis isomers, respectively, each present as a 1/1 mixture of amide rotamers.
15. 8. We thank H. Bieräugel and U.K. Pandit of the University of Amsterdam (The Netherlands) for these unpublished observations.
16. 3CN) δ 7.34 (m, 2H), 7.27 (m, 1H), 7.22 (m, 2H), 4.73 (d, J=15.0, 1H), 4.64 (dd, J=9.9, J=5.3, 1H), 4.30 (d, J=15.0, 1H), 4.19 (qd, J=7.1, J=2.0, 2H), 3.60 (s, 3H), 3.26 (m, 2H), 2.63 (dd, J=13.7, J=5.3, 1H), 2.58 (dd, J=16.1, J=4.5, 1H), 2.41 (om, 2H), 2.37 (dd, J=13.7, J=9.9, 1H), 2.19 (dd, J=16.1, J=9.0, 1H), 2.14 (om, 1H), 1.80 (ddd, J=13.7, J=3.9, J=3.4, 1H), 1.46 (s, 9H), 1.24 1.24 (t, J=7.1, 3H).
17. 10. For an alternative preparation of 11: Hirai, Y.; Terada, T.; Yamazaki, T.; Momose, T. J. Chem. Soc. Perkin Tr. 1, 1992, 509-516.
18. 11. Corey, E.J.; Fuchs, P.L. Tetrahedron Lett., 1972, 3769-3772.
19. 12. It is of interest to note that the β,γ isomer was only hydrogenated at an acceptable rate in the presence of large excess of the 10% Pd/C catalyst (substrate/dry catalyst 2/1 w/w).
20. 13 The following NOE interactions were determined for 12 and 15. (equation presented)
21. 2) d 193.3, 171.1, 169.7, 164.4, 138.0, 129.1, 128.6, 128.0, 107.2, 61.9, 59.7, 51.9, 50.2, 43.9, 38.6, 38.4, 37.6, 26.1, 23.8, 22.1, 14.5, 14.4.