Architectural self-construction in nature and chemical synthesis

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 15, 2003, Pages 3225-3228

  Sorensen, Erik J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FR 182877; NATURAL PRODUCT; OXIDE; POLYCYCLIC HYDROCARBON; SQUALENE OXIDE; UNCLASSIFIED DRUG;

BIOMIMETICS; CHEMISTRY; CYTOTOXICITY; DIELS ALDER REACTION; DRUG ACTIVITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; MOLECULE; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038016568     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00185-8     Document Type: Short Survey

References (55)

1. (a) For reviews and discussions, see: Lindsey J.S., New J. Chem. 15:1991;153 (b) Klug A. Angew. Chem. Int. Ed. 22:1983;565 (c) Michl J. Chemical synthesis: gnosis to prognosis. Chatgilialoglu C., Snieckus V. 1996;429 Kluwer Academic Publishers, Boston, (d) Eschenmoser, A. In Pontificiae Academiae Scientiarum Scripta Varia No. 99, Proceed. Jubilee Plenary Session 'Science and the Future of Mankind', Ex Aedibys Academics in Civitate Vaticana, 2001, p 235. (e) Eschenmoser A., Loewenthal E. Chem. Soc. Rev. 1992;1.
2. (a) For reviews and discussions, see: Lindsey J.S., New J. Chem. 15:1991;153 (b) Klug A. Angew. Chem. Int. Ed. 22:1983;565 (c) Michl J. Chemical synthesis: gnosis to prognosis. Chatgilialoglu C., Snieckus V. 1996;429 Kluwer Academic Publishers, Boston, (d) Eschenmoser, A. In Pontificiae Academiae Scientiarum Scripta Varia No. 99, Proceed. Jubilee Plenary Session 'Science and the Future of Mankind', Ex Aedibys Academics in Civitate Vaticana, 2001, p 235. (e) Eschenmoser A., Loewenthal E. Chem. Soc. Rev. 1992;1.
3. (a) For reviews and discussions, see: Lindsey J.S., New J. Chem. 15:1991;153 (b) Klug A. Angew. Chem. Int. Ed. 22:1983;565 (c) Michl J. Chemical synthesis: gnosis to prognosis. Chatgilialoglu C., Snieckus V. 1996;429 Kluwer Academic Publishers, Boston, (d) Eschenmoser, A. In Pontificiae Academiae Scientiarum Scripta Varia No. 99, Proceed. Jubilee Plenary Session 'Science and the Future of Mankind', Ex Aedibys Academics in Civitate Vaticana, 2001, p 235. (e) Eschenmoser A., Loewenthal E. Chem. Soc. Rev. 1992;1.
4. (a) For reviews and discussions, see: Lindsey J.S., New J. Chem. 15:1991;153 (b) Klug A. Angew. Chem. Int. Ed. 22:1983;565 (c) Michl J. Chemical synthesis: gnosis to prognosis. Chatgilialoglu C., Snieckus V. 1996;429 Kluwer Academic Publishers, Boston, (d) Eschenmoser, A. In Pontificiae Academiae Scientiarum Scripta Varia No. 99, Proceed. Jubilee Plenary Session 'Science and the Future of Mankind', Ex Aedibys Academics in Civitate Vaticana, 2001, p 235. (e) Eschenmoser A., Loewenthal E. Chem. Soc. Rev. 1992;1.
5. (a) For reviews and discussions, see: Lindsey J.S., New J. Chem. 15:1991;153 (b) Klug A. Angew. Chem. Int. Ed. 22:1983;565 (c) Michl J. Chemical synthesis: gnosis to prognosis. Chatgilialoglu C., Snieckus V. 1996;429 Kluwer Academic Publishers, Boston, (d) Eschenmoser, A. In Pontificiae Academiae Scientiarum Scripta Varia No. 99, Proceed. Jubilee Plenary Session 'Science and the Future of Mankind', Ex Aedibys Academics in Civitate Vaticana, 2001, p 235. (e) Eschenmoser A., Loewenthal E. Chem. Soc. Rev. 1992;1.
6. (a) Langdon R.G., Bloch K. J. Biol. Chem. 200:1953;135.
7. (b) Woodward R.B., Bloch K. J. Am. Chem. Soc. 75:1953;2023.
8. (c) Eschenmoser A., Ruzicka L., Jeger O., Arigoni D. Helv. Chim. Acta. 38:1955;1890.
9. (d) Stork G., Burgstahler A.W. J. Am. Chem. Soc. 77:1955;5068.
10. (e) Corey E.J., Russey W.E., Ortiz de Montellano P.R. J. Am. Chem. Soc. 88:1966;4750.
11. (f) van Tamelen E.E., Willett J.D., Clayton R.B., Lord K.E. J. Am. Chem. Soc. 88:1966;4752.
12. (g) Clayton R.B. Quart. Rev. Chem. Soc. 19:1965;168.
13. (h) Cornforth J.W. Pure Appl. Chem. 2:1961;607.
14. Sorensen E.J. Helv. Chim. Acta. 83:2000;1673.
15. (a) Johnson W.S. Acc. Chem. Res. 1:1968;1.
16. (b) Johnson W.S. Angew. Chem. Int. Ed. 15:1976;9.
17. (c) Johnson W.S. Bioorg. Chem. 5:1976;51.
18. (d) van Tamelen E.E. Acc. Chem. Res. 8:1975;152
19. (e) van Tamelen E.E. Pure Appl. Chem. 53:1981;1259.
20. Nicolaou K.C., Petasis N.A. Strategies and Tactics In Organic Synthesis, Vol. 1. Lindberg T. 1984;155 Academic Press, San Diego.
21. Heathcock C.H. Proc. Natl. Acad. Sci. U.S.A. 93:1996;14323.
22. (a) Robinson R. J. Chem. Soc. 1917;762.
23. (b) For syntheses of the tropane alkaloids, pseudopelletierine, lobelanine, and related bases under physiological conditions, see: Schöpf C., Lehmann G. Liebigs Ann. Chem. 518:1935;1.
24. (c) For a recent review of biomimetic syntheses of alkaloids, see: Scholz U., Winterfeldt E. Nat. Prod. Rep. 17:2000;349.
25. Presentation speech by Professor A. Fredga on the occasion of Sir Robert Robinson's receipt of the Nobel Prize in Chemistry in 1947, see: Nobel Lectures: Chemistry 1942-1962; The Nobel Foundation; Elsevier: New York, 1964, p. 163.
26. For an excellent, early review of 'biogenetic-type' syntheses, see: van Tamelen E.E. Fortschr. Chem. Org. Naturst. 19:1961;242.
27. Woodward's synthesis of chlorophyll established a link between the porphyrins and the chlorins, two ancient and biochemically significant classes of natural products. Woodward R.B. Pure Appl. Chem. 2:1961;383.
28. For a discussion of the etiological aspect of Woodward's chlorophyll synthesis, see: Eschenmoser, A. In Robert Burns Woodward: Architect and Artist in the World of Molecules, Benfey, O. T.; Morris, P. J. T., Eds., Chemical Heritage Foundation: Philadelphia, 2001, ch. 4, p 23.
29. 12 'self-assemble' with surprising ease under appropriate conditions. For discussions, see: Eschenmoser A. Angew. Chem. Int. Ed. 27:1988;5.
30. (a) Vosburg D.A., Vanderwal C.D., Sorensen E.J. J. Am. Chem. Soc. 124:2002;4552.
31. (b) Vanderwal C.D., Vosburg D.A., Weiler S., Sorensen E.J. J. Am. Chem. Soc. 125:2003;5393.
32. (a) Sato B., Muramatsu H., Miyauchi M., Hori Y., Takase S., Hino M., Hashimoto S., Terano H. J. Antibiot. 53:2000;123.
33. (b) Sato B., Nakajima H., Hori Y., Hino M., Hashimoto S., Terano H. J. Antibiot. 53:2000;204
34. (c) Yoshimura S., Sato B., Kinoshita T., Takase S., Terano H. J. Antibiot. 53:2000;615.
35. For a recent review of transannular Diels-Alder reactions, see: Marsault E., Toró A., Nowak P., Deslongchamps P. Tetrahedron. 57:2001;4243.
36. For a recent biomimetic natural product synthesis featuring intermolecular and transannular Diels-Alder reactions, see: Layton M.E., Morales C.A., Shair M.D. J. Am. Chem. Soc. 124:2002;773.
37. For a recent review of biosynthetic Diels-Alder reactions, see: Stocking, E. M.; Williams, R. M. Angew. Chem. Int. Ed. 2002, in press.
38. (a) Trost B.M., Brickner S.J. J. Am. Chem. Soc. 105:1983;568.
39. (b) Trost B.M. Angew. Chem. Int. Ed. 28:1989;1173.
40. Soon after we described our synthesis of (+)-FR182877 (see reference 12), the Evans laboratory described a synthesis of (-)-FR182877 by an approach that also featured tandem transannular Diels-Alder reactions, see: Evans D.A., Starr J.T. Angew. Chem. Int. Ed. 41:2002;1787.
41. Höfs R., Walker M., Zeeck A. Angew. Chem. Int. Ed. 39:2000;3258.
42. (a) Cane D.E., Walsh C.T., Khosla C. Science. 282:1998;63.
43. (b) Khosla C. Chem. Rev. 97:1997;2577.
44. (c) Pohl N. J. Chem. Ed. 77:2000;1421.
45. (d) Schneider T., Walsh C.T., O'Connor S.E. J. Am. Chem. Soc. 124:2002;11272.
46. (a) Reggelin M., Brenig V. Tetrahedron Lett. 37:1996;6851.
47. (b) Paterson I., Scott J.P. Tetrahedron Lett. 38:1997;7441.
48. (c) Paterson I., Scott J.P. Tetrahedron Lett. 38:1997;7445.
49. (d) Gennari C., Ceccarelli S., Piarulli U., Aboutayab K., Donghi M., Paterson I. Tetrahedron. 54:1998;14999.
50. (e) Reggelin M., Brenig V., Welcker R. Tetrahedron Lett. 39:1998;4801.
51. (f) Paterson I., Donghi M., Gerlach K. Angew. Chem. Int. Ed. 39:2000;3315.
52. (g) Arjona O., Menchaca R., Plumet J. J. Org. Chem. 66:2001;2400.
53. (h) Harrison B., Verdine G. Org. Lett. 3:2001;2157.
54. (i) Harrison B.A., Gierasch T.M., Neilan C., Pasternak G.W., Verdine G.L. J. Am. Chem. Soc. 124:2002;13352
55. (j) Paterson I., Temai-Laib T. Org. Lett. 4:2002;2473.