Claisen orthoester rearrangement in the direct preparation of deplancheine derivatives possessing a malonyl group at C-15

Heterocycles

Volumn 43, Issue 9, 1996, Pages 1981-1989

  Lounasmaa, Mauri ^a   Hanhinen, Pirjo ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011957808     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7538     Document Type: Article

References (25)

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2. G. B. Bennett, Synthesis, 1977, 589.
3. S. Blechert, synthesis, 1989, 71.
4. F. E. Ziegler, Acc. Chem. Res., 1977, 10, 227.
5. J. Seyden-Penne, "Synthèse et Catalyse Asymétriques" , InterÉditions/ CNRS Éditions, Paris, 1994, pp. 464-470.
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8. M. Lounasmaa, P. Hanhinen, and R. Jokela, Tetrahedron, 1995, 51, 8623.
9. Biogenetic numbering. J. Le Men and W. I. Taylor, Experientia, 1965, 21, 508.
10. M. Lounasmaa and A. Tolvanen, "The Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, 2nd Ed., Wiley, New York, 1994, pp. 57-159.
11. A. Pinner, Ber. 1883, 16, 352 and 1643. See also, R. H. DeWolfe, Synthesis, 1974, 153.
12. A. Pinner, Ber. 1883, 16, 352 and 1643. See also, R. H. DeWolfe, Synthesis, 1974, 153.
13. S. M. McElvain and J. P. Schroeder, J. Am. Chem. Soc. , 1949, 71, 40.
14. Aldrich, Compound 24, 120-2.
15. Aldrich, Compound 10, 842-1.
16. In conformity with our general presentation of the indoloquinolizidines under examination, compounds (1 - 2), (10 -11), and (15 - 18) are drawn in such a way that their relative configurations become 3S*,19R* and 3S*,19S*, respectively. This is done despite the convention that the centre of chirality, which is first cited and which has the lowest locant, generally is presented in such a way that its chirality descriptor becomes R*. "A Guide to IUPAC Nomenclature of Organic Compounds", Recommendations 1993, ed. by R. Panico, W. H. Powell, and J.-C. Richer, Blackwell Scientific Publications, Oxford, 1993, p. 154.
17. Racemic compound (13) is identical with racemic compound (13′). Since compound (13) is formed by the Claisen rearrangement from the vinyl allyl ether (10), for mechanistic reasons we prefer its presentation as shown, even though the C-15-H in formula (13), being β, is unnatural. Likewise, the same situation holds for compound (14).
18. R. Jokela, M. Halonen, and M. Lounasmaa, Tetrahedron, 1993, 49, 2567.
19. M. Lounasmaa, R. Jokela, P. Hanhinen, J. Miettinen, and J. Salo, Tetrahedron, 1994, 50, 9207.
20. M. Lounasmaa, R. Jokela, P. Hanhinen, J. Miettinen, and J. Salo, J. Nat. Prod., 1995, 58, 131.
21. M. Lounasmaa, R. Jokela, M. Back, P. Hanhinen, and C. Laine, Tetrahedron, 1995, 51, 11891. Note! The C-19 assignments (R* v. S*) of compounds 1 (1a, 1b) - 2 (2a, 2b) are erroneous and should be interchanged.
22. 18,19,22-24
23. M. Lounasmaa, R. Jokela, J. Miettinen, and M. Halonen, Heterocycles, 1992, 34, 1497.
24. M. Lounasmaa, R. Jokela, M. Halonen, and J. Miettinen, Heterocycles, 1993, 36, 2523.
25. M. Lounasmaa, R. Jokela, U. Anttila, P. Hanhinen, and C. Laine, Tetrahedron, 1996, 52, 6803.