A spontaneous bicyclization facilitates a synthesis of (-)-hispidospermidin

Tetrahedron

Volumn 59, Issue 35, 2003, Pages 6921-6932

  Tamiya, Junko ^a   Sorensen, Erik J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Biomimetic synthesis; Hispidospermidin; Proximity; cyclization

Indexed keywords

ACID; ALDEHYDE; ALKENE DERIVATIVE; HISPIDOSPERMIDIN; PHOSPHOLIPASE C INHIBITOR; SPIRO[4.5]DECA 1,7 DIENE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; CYCLIZATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0041657471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00936-0     Document Type: Article

References (79)

1. Woodward R.B. Pure Appl. Chem. 17:1968;545.
2. Jencks W.P. Catalysis in Chemistry and Enzymology. 1969;Dover, New York. Chapter 1, pp 7-41.
3. (a) Yanagisawa M., Sakai A., Adachi K., Sano T., Watanabe K., Tanaka Y., Okuda T. J. Antibiot. 47:1994;1-5
4. (b) Ohtsuka T., Itezono Y., Nakayama N., Sakai A., Shimma N., Yokose K., Seto H. J. Antibiot. 47:1994;6-15.
5. (a) Hokin L.E. Annu. Rev. Biochem. 54:1985;205-235
6. (b) Noh D.Y., Shin S.H., Rhee S.G. Biochim. Biophys. Acta. 1242:1995;1099-1141
7. (c) Schlessinger J. Proc. Natl. Acad. Sci. USA. 94:1997;2798-2799.
8. (a) Frontier A.J., Raghavan S., Danishefsky S.J. J. Am. Chem. Soc. 119:1997;6686-6687
9. (b) Frontier A.J., Raghavan S., Danishefsky S.J. J. Am. Chem. Soc. 122:2000;6151-6159.
10. Overman L.E., Tomasi A.L. J. Am. Chem. Soc. 120:1998;4039-4040.
11. (a) Tamiya J., Sorensen E.J. J. Am. Chem. Soc. 122:2000;9556-9557 Tamiya, J. Ph.D. Thesis, The Scripps Research Institute, 2002.
12. Ellis D.A., Hart D.J., Zhao L. Tetrahedron Lett. 41:2000;9357-9360.
13. Ruzicka L., Eschenmoser A., Heusser H. Experientia. 9:1953;357-367.
14. (a) Parker W., Roberts J.S., Ramage R. Quart. Rev., Chem. Soc. 21:1967;331-363. Cyclization of trans,trans-farnesyl pyrophosphate ( 2 ) to γ(-bisabolene ( 3 ) presupposes an initial isomerization of 2 to nerolidyl pyrophosphate or alternatively to cis,trans-farnesyl pyrophosphate.
15. For discussions, see: (a) Cane D.E. Acc. Chem. Res. 18:1985;220-226 (c) Andersen N.H., Syrdal D.D. Tetrahedron Lett. 13:1972;2455-2458.
16. For discussions, see: (a) Cane D.E. Acc. Chem. Res. 18:1985;220-226 (c) Andersen N.H., Syrdal D.D. Tetrahedron Lett. 13:1972;2455-2458.
17. (a) Hoesch K. Ber. Dtsch. Chem. Ges. 48:1915;1122-1133
18. (b) Houben J. Ber. Dtsch. Chem. Ges. 59:1926;2878-2891
19. (c) Conley R.T., Lange R.J. J. Org. Chem. 28:1963;210-214
20. (d) Yato M., Ohwada T., Shudo K. J. Am. Chem. Soc. 113:1991;691-692
21. (e) Sato Y., Yato M., Ohwada T., Saito S., Shudo K. J. Am. Chem. Soc. 117:1995;3037-3043.
22. For reviews of radical cyclizations, see: (a) Curran D.P. Synthesis. 1988;417-439 (b) Curran D.P. Synthesis. 1988;489-513 (c) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (d) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. (N.Y.). 48:1996;301-856.
23. For reviews of radical cyclizations, see: (a) Curran D.P. Synthesis. 1988;417-439 (b) Curran D.P. Synthesis. 1988;489-513 (c) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (d) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. (N.Y.). 48:1996;301-856.
24. For reviews of radical cyclizations, see: (a) Curran D.P. Synthesis. 1988;417-439 (b) Curran D.P. Synthesis. 1988;489-513 (c) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (d) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. (N.Y.). 48:1996;301-856.
25. For reviews of radical cyclizations, see: (a) Curran D.P. Synthesis. 1988;417-439 (b) Curran D.P. Synthesis. 1988;489-513 (c) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (d) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. (N.Y.). 48:1996;301-856.
26. Corey E.J., Ensley H.E., Suggs J.W. J. Org. Chem. 41:1976;380-381.
27. Corey E.J., Boger D.L. Tetrahedron Lett. 19:1978;2461-2464.
28. (a) Marx J.N., Norman L.R. Tetrahedron Lett. 14:1973;4375-4378
29. (b) Marx J.N., Norman L.R. J. Org. Chem. 40:1975;1602-1606
30. (c) Sattelkau T., Hollman C., Eilbracht P. Synlett. 1996;1221-1223.
31. (a) Cusack N.J., Reese C.B., Risius A.C., Roozpeikar B. Tetrahedron. 32:1976;2157-2162
32. (b) Chamberlin A.R., Liotta E.L., Bond F.T. Org. Synth. 61:1983;141-146.
33. Shapiro R.H. Org. React. (N.Y.). 23:1975;405.
34. (a) Chamberlin A.R., Stemke J.E., Bond F.T. J. Org. Chem. 43:1978;147-154
35. (b) Chamberlin A.R., Bloom S.H. Org. React. (N.Y.). 39:1990;1-83.
36. Nahm S., Weinreb S.M. Tetrahedron Lett. 22:1981;3815-3818.
37. (a) Mahoney W.S., Brestensky D.M., Stryker J.M. J. Am. Chem. Soc. 110:1988;291-293
38. (b) Brestensky D.M., Stryker J.M. Tetrahedron Lett. 30:1989;5677-5680
39. (c) Koenig T.M., Daueble J.F., Brestensky D.M., Stryker J.M. Tetrahedron Lett. 31:1990;3237-3240.
40. Kirsten C.N., Herm M., Schrader T.H. J. Org. Chem. 62:1997;6882-6887.
41. (a) McKenzie A. J. Chem. Soc. 85:1904;1249-1262
42. (b) McKenzie A. J. Chem. Soc. 89:1906;365-383.
43. Morrison J.D., Mosher H.S. Asymmetric Organic Reactions. 1976;American Chemical Society, Washington, DC. Chapter 2, pp 50-83.
44. (a) Prelog V. Helv. Chim. Acta. 36:1953;308-319
45. (b) Prelog V., Meier H.L. Helv. Chim. Acta. 36:1953;320-325
46. (c) Dauben W.G., Dickel D.F., Jeger O., Prelog V. Helv. Chim. Acta. 36:1953;325-335
47. (d) Prelog V., Ceder O., Wilhelm M. Helv. Chim. Acta. 38:1955;303-312.
48. (a) Corey E.J., Ensley H.E. J. Am. Chem. Soc. 97:1975;6908-6909
49. (b) Corey E.J. Angew. Chem. Int. Ed. 41:2002;1650-1667.
50. Ort O. Organic Syntheses. Collective Vol. 8:1993;Wiley, New York. pp 522-528.
51. (a) Whitesell J.K., Deyo D., Bhattacharya A. J. Chem. Soc., Chem Commun. 1983;802
52. (b) Whitesell J.K., Buchanan C.M. J. Org. Chem. 51:1986;5443-5445.
53. White J.D., Somers T.C. J. Am. Chem. Soc. 109:1987;4424-4426.
54. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
55. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
56. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
57. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
58. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
59. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
60. For reviews of the carbonyl ene and Prins reactions, see: (a) Adams D.R., Bhatnagar S.P. Synthesis. 1977;661-672 (b) Snider B.B. Acc. Chem. Res. 13:1980;426-432 (c) Snider B.B. Trost B.M., Fleming I. Comprehensive Organic Syntheses: Additions to C-X π-Bonds, Part 2. vol. 2:1991;527-561 Pergamon, Oxford. Chapter 2.1 (d) Whitesell J.K. Stereoselective Synthesis, Houben-Weyl. vol. 5:1996;Thieme, New York. pp 3271-3297. For selected mechanistic studies, see: (e) Snider B.B., Ron E. J. Am. Chem. Soc. 107:1985;8160-8164 (f) Song Z., Beak P. J. Am. Chem. Soc. 112:1990;8126-8134 (g) Marshall J.A., Andersen M.W. J. Org. Chem. 57:1992;5851-5856.
61. (a) Lipshutz B.H., Pegram J.J. Tetrahedron Lett. 21:1980;3343-3346
62. (b) Lipshutz B.H., Moretti R., Crow R. Tetrahedron Lett. 30:1989;15-18.
63. (a) Mancuso A.J., Huang S.-L., Swern D. J. Org. Chem. 43:1978;2480-2482
64. (b) Omura K., Swern D. Tetrahedron. 34:1978;1651-1660
65. (c) Mancuso A.J., Swern D. Synthesis. 1981;165-185
66. (d) Tidwell T.T. Org. React. (N.Y.). 39:1990;297-572.
67. (a) Marshall J.A., Andersen N.H., Johnson P.C. J. Org. Chem. 35:1970;186-191
68. (b) Marshall J.A., Andersen N.H., Schlicher J.W. J. Org. Chem. 35:1970;858-861
69. (c) Marshall J.A., Wuts P.G.M. J. Org. Chem. 42:1977;1794-1798.
70. For a review of the imino ene reaction, see: Borzilleri R.M., Weinreb S.M. Synthesis. 1995;347-360.
71. (a) Stork G., Kahne D.E. J. Am. Chem. Soc. 105:1983;1072-1073 (b) Schultz A.G., McCloskey P.J. J. Org. Chem. 50:1985;5905-5907 (c) Brown J.M., Naik R.G. J. Chem. Soc., Chem. Commun. 1982;348-350. For a comprehensive review of substrate-directed reactions, see: Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370.
72. (a) Stork G., Kahne D.E. J. Am. Chem. Soc. 105:1983;1072-1073 (b) Schultz A.G., McCloskey P.J. J. Org. Chem. 50:1985;5905-5907 (c) Brown J.M., Naik R.G. J. Chem. Soc., Chem. Commun. 1982;348-350. For a comprehensive review of substrate-directed reactions, see: Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370.
73. (a) Stork G., Kahne D.E. J. Am. Chem. Soc. 105:1983;1072-1073 (b) Schultz A.G., McCloskey P.J. J. Org. Chem. 50:1985;5905-5907 (c) Brown J.M., Naik R.G. J. Chem. Soc., Chem. Commun. 1982;348-350. For a comprehensive review of substrate-directed reactions, see: Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370.
74. (a) Stork G., Kahne D.E. J. Am. Chem. Soc. 105:1983;1072-1073 (b) Schultz A.G., McCloskey P.J. J. Org. Chem. 50:1985;5905-5907 (c) Brown J.M., Naik R.G. J. Chem. Soc., Chem. Commun. 1982;348-350. For a comprehensive review of substrate-directed reactions, see: Hoveyda A.H., Evans D.A., Fu G.C. Chem. Rev. 93:1993;1307-1370.
75. (a) Thompson H.W., Wong J.K. J. Org. Chem. 50:1985;4270-4276
76. (b) Thompson H.W., McPherson E. J. Org. Chem. 42:1977;3350-3353
77. (c) Thompson H.W., Naipawer R.E. J. Am. Chem. Soc. 95:1973;6379-6386.
78. For a review of reductions using metal borides and aluminides, see: Ganem B., Osby J.O. Chem. Rev. 86:1986;763-780. See also: Ipaktschi J. Chem. Ber. 117:1984;856-858.
79. For a review of reductions using metal borides and aluminides, see: Ganem B., Osby J.O. Chem. Rev. 86:1986;763-780. See also: Ipaktschi J. Chem. Ber. 117:1984;856-858.