The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7823-7826

  Birkbeck, Anthony A ^a   Enders, Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; IODIDE; NATURAL PRODUCT; PECTINATONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; TECHNIQUE;

EID: 0032558637     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01742-0     Document Type: Article

References (38)

1. [1] Ishiwata H, Nemoto T, Ojika M, Yamada K. J. Org. Chem. 1994;59:4710-4711. Devys M, Ferezou J-P, Topgi RS, Barbier M, Bousquet J-F, Kollmann A. J. Chem. Soc. Perkin Trans. 1. 1984:2133-2137. Capon RJ, Faulkner DJ. J. Org. Chem. 1984;49:2506-2508.
2. [1] Ishiwata H, Nemoto T, Ojika M, Yamada K. J. Org. Chem. 1994;59:4710-4711. Devys M, Ferezou J-P, Topgi RS, Barbier M, Bousquet J-F, Kollmann A. J. Chem. Soc. Perkin Trans. 1. 1984:2133-2137. Capon RJ, Faulkner DJ. J. Org. Chem. 1984;49:2506-2508.
3. [1] Ishiwata H, Nemoto T, Ojika M, Yamada K. J. Org. Chem. 1994;59:4710-4711. Devys M, Ferezou J-P, Topgi RS, Barbier M, Bousquet J-F, Kollmann A. J. Chem. Soc. Perkin Trans. 1. 1984:2133-2137. Capon RJ, Faulkner DJ. J. Org. Chem. 1984;49:2506-2508.
4. [2] Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986;27:4713-4716. Ishiwata H, Sone H, Kigoshi H, Yamada K. J. Org. Chem. 1994;59:4712-4713. Schlessinger RH, Gillman KW. Tetrahedron Lett. 1996;37:1331-1334. Stroermer D, Caron S, Heathcock, CH, J. Org. Chem. 1996;61:9115-9125. Tomooka K, Nagasawa A, Wei S-Y, Nakai T. Tetrahedron Lett. 1996;37:8895-8898.
5. [2] Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986;27:4713-4716. Ishiwata H, Sone H, Kigoshi H, Yamada K. J. Org. Chem. 1994;59:4712-4713. Schlessinger RH, Gillman KW. Tetrahedron Lett. 1996;37:1331-1334. Stroermer D, Caron S, Heathcock, CH, J. Org. Chem. 1996;61:9115-9125. Tomooka K, Nagasawa A, Wei S-Y, Nakai T. Tetrahedron Lett. 1996;37:8895-8898.
6. [2] Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986;27:4713-4716. Ishiwata H, Sone H, Kigoshi H, Yamada K. J. Org. Chem. 1994;59:4712-4713. Schlessinger RH, Gillman KW. Tetrahedron Lett. 1996;37:1331-1334. Stroermer D, Caron S, Heathcock, CH, J. Org. Chem. 1996;61:9115-9125. Tomooka K, Nagasawa A, Wei S-Y, Nakai T. Tetrahedron Lett. 1996;37:8895-8898.
7. [2] Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986;27:4713-4716. Ishiwata H, Sone H, Kigoshi H, Yamada K. J. Org. Chem. 1994;59:4712-4713. Schlessinger RH, Gillman KW. Tetrahedron Lett. 1996;37:1331-1334. Stroermer D, Caron S, Heathcock, CH, J. Org. Chem. 1996;61:9115-9125. Tomooka K, Nagasawa A, Wei S-Y, Nakai T. Tetrahedron Lett. 1996;37:8895-8898.
8. [2] Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett. 1986;27:4713-4716. Ishiwata H, Sone H, Kigoshi H, Yamada K. J. Org. Chem. 1994;59:4712-4713. Schlessinger RH, Gillman KW. Tetrahedron Lett. 1996;37:1331-1334. Stroermer D, Caron S, Heathcock, CH, J. Org. Chem. 1996;61:9115-9125. Tomooka K, Nagasawa A, Wei S-Y, Nakai T. Tetrahedron Lett. 1996;37:8895-8898.
9. [3] Evans DA, Dow RL, Shih TL, Takacs JM, Zahler R. J. Am. Chem. Soc. 1990;112:5290-5313.
10. [4] White JD, Johnson AT. J. Org. Chem. 1994;59:3347-3358. Decicco CP, Grover P. J. Org. Chem. 1996;61:3534-3541.
11. [4] White JD, Johnson AT. J. Org. Chem. 1994;59:3347-3358. Decicco CP, Grover P. J. Org. Chem. 1996;61:3534-3541.
12. [5] Abiko A, Masamune S. Tetrahedron Lett. 1996;37:1081-1084.
13. [6] Myers AG, Yang BH, Chen H, Kopecky DJ. Synlett 1997:457-459. Myers AG, Yang BH, Chen H, McKinstry L, Kopecky DJ, Gleason JL. J. Am. Chem. Soc. 1997;119:6496-6511.
14. [6] Myers AG, Yang BH, Chen H, Kopecky DJ. Synlett 1997:457-459. Myers AG, Yang BH, Chen H, McKinstry L, Kopecky DJ, Gleason JL. J. Am. Chem. Soc. 1997;119:6496-6511.
15. [7] Enders D, Tiebes J, De Kimpe N, Keppens M, Stevens C, Smagghe G, Betz O. J. Org. Chem. 1993;58:4881-4884. Nicolaou KC, Yue EW, Naniwa Y, De Riccardis F, Nadin A, Leresche JE, La Greca S, Yang Z. Angew. Chem. Int. Ed. Engl. 1994;33:2184-2187. Nicolaou KC, Yue EW, La Greca S, Nadin A, Yang Z, Leresche JE, Tsuri T, Naniwa Y, De Riccardis F. Chem. Eur. J. 1995;1:467-494.
16. [7] Enders D, Tiebes J, De Kimpe N, Keppens M, Stevens C, Smagghe G, Betz O. J. Org. Chem. 1993;58:4881-4884. Nicolaou KC, Yue EW, Naniwa Y, De Riccardis F, Nadin A, Leresche JE, La Greca S, Yang Z. Angew. Chem. Int. Ed. Engl. 1994;33:2184-2187. Nicolaou KC, Yue EW, La Greca S, Nadin A, Yang Z, Leresche JE, Tsuri T, Naniwa Y, De Riccardis F. Chem. Eur. J. 1995;1:467-494.
17. [7] Enders D, Tiebes J, De Kimpe N, Keppens M, Stevens C, Smagghe G, Betz O. J. Org. Chem. 1993;58:4881-4884. Nicolaou KC, Yue EW, Naniwa Y, De Riccardis F, Nadin A, Leresche JE, La Greca S, Yang Z. Angew. Chem. Int. Ed. Engl. 1994;33:2184-2187. Nicolaou KC, Yue EW, La Greca S, Nadin A, Yang Z, Leresche JE, Tsuri T, Naniwa Y, De Riccardis F. Chem. Eur. J. 1995;1:467-494.
18. [8] Enders D, Eichenauer H. Tetrahedron Lett. 1977;2:191-194. Enders D, Eichenauer H. Chem. Ber. 1979;112:2933-2960.
19. [8] Enders D, Eichenauer H. Tetrahedron Lett. 1977;2:191-194. Enders D, Eichenauer H. Chem. Ber. 1979;112:2933-2960.
20. [9] Control quench experiments: 1 mmol scale, 0.5 M hydrazone in THF at 0° and addition of n-propyl iodide at 0. Similiarly subsequent experiments showed that deprotonation using LDA (1 mmol hydrazone, 0.5M THF, 0°, and alkylation at 0°) was complete in less than 45 minutes.
21. 1H NMR). Similar results have been obtained for ketone SAMP-hydrazones, Job A, unpublished results. See also: Kawanami Y, Ito Y, Kitigawa T, Taniguchi Y, Katsuki T, Yamaguchi M. Tetrahedron Lett. 1984;25:857-860.
22. [11] Enders D, Zamponi A, Raabe G. Synlett. 1992:897-900.
23. 1H NMR analysis (500 MHz) indicated no detectable racemization during this procedure.
24. [13] For possibly related observations see: Netscher T, Bohrer P. Tetrahedron Lett. 1996;37:8359-8362. The sulfinate ester was isolated as a 1:1 mixture of diastereoisomers. (equation presented)
25. [14] Raber DJ, Guida WC. J. Org. Chem. 1976;41:690-696.
26. [15] The use of TBAI, Nal, KI in 30% DMPU in THF to effect the displacement and the addition of the preformed aza-enolate of A in THF reduced the selectivity to between 5:1 and 2:1.
27. [16] The addition of this volume of pentane had no detectable effect on the stereochemistry of the alkylation reaction.
28. [17] All attempts to recrystallise the mixture to increase the diastereomeric purity from a variety of solvents were unsuccessful.
29. [18] Nahm S, Weinreb SM. Tetrahedron Lett. 1981;22:3815-3818.
30. [19] Williams JM, Jobson RB, Yasuda N, Marchesini G, Dolling U-H, Grabowski EJJ. Tetrahedron Lett. 1995;36:5461-5464.
31. 3). Biskupiak JE, Ireland CM. Tetrahedron Lett. 1983; 24:3055-3058. Norte M, Cataldo F, Gonzalez AG, Rodriguez ML, Ruiz-Perez C. Tetrahedron 1990; 46:1669-1678. Garson MJ, Small CJ, Skelton BW, Thinapong P, White AH, J. Chem. Soc. Perkin Trans, 1. 1990:805-807.
32. 3). Biskupiak JE, Ireland CM. Tetrahedron Lett. 1983; 24:3055-3058. Norte M, Cataldo F, Gonzalez AG, Rodriguez ML, Ruiz-Perez C. Tetrahedron 1990; 46:1669-1678. Garson MJ, Small CJ, Skelton BW, Thinapong P, White AH, J. Chem. Soc. Perkin Trans, 1. 1990:805-807.
33. 3). Biskupiak JE, Ireland CM. Tetrahedron Lett. 1983; 24:3055-3058. Norte M, Cataldo F, Gonzalez AG, Rodriguez ML, Ruiz-Perez C. Tetrahedron 1990; 46:1669-1678. Garson MJ, Small CJ, Skelton BW, Thinapong P, White AH, J. Chem. Soc. Perkin Trans, 1. 1990:805-807.
34. [21] Huckin SN, Weiler L. J. Am. Chem. Soc. 1974;96:1082-1087.
35. [22] Hanamoto T, Hiyama T. Tetrahedron Lett. 1988;29:6467-6470.
36. [23] Ishibashi Y, Ohba S, Nishiyama S, Yamamura S. Tetrahedron Lett. 1996;37:2997-3000. See also reference 2.
37. [24] Norte M, Fernandez JJ, Padilla A. Tetrahedron Lett. 1994; 35:3413-3416. Paul MC, Zubia E, Ortega MJ, Salva J. Tetrahedron. 1997;53:2303-2308.
38. [24] Norte M, Fernandez JJ, Padilla A. Tetrahedron Lett. 1994; 35:3413-3416. Paul MC, Zubia E, Ortega MJ, Salva J. Tetrahedron. 1997;53:2303-2308.