[2.2.1]-Bicyclic systems relevant to synthetic studies on CP-225,917 - Use of a new silylated cyclopentadiene

Tetrahedron

Volumn 60, Issue 19, 2004, Pages 4205-4221

  Clive, Derrick L J ^a   Cheng, Hua ^a   Gangopadhyay, Pulak ^a   Huang, Xiaojun ^a   Prabhudas, Bodhuri ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

2.2.1 Bicyclic ketone; Boron trifluoride etherate acetic acid; Diels Alder reaction; Modified Tamao Fleming oxidation; Silylated cyclopentadiene

Indexed keywords

7 [(4 METHOXYPHENYL)DIMETHYLSILANYL]BICYCLO[2.2.1]HEPT 5 ENE 2,3 DICARBOXYLIC ACID DIMETHYL ESTER; 7 HYDROXYBICYCLO[2.2.1]HEPT 5 ENE 2,3 DICARBOXYLIC ACID DIMETHYL ESTER; ALCOHOL DERIVATIVE; BENZOIC ACID 6 [1,3]DITHIAN 2 YL 5 (OCT 6 ENYL) 7 OXOBICYCLO[2.2.1]HEPT 2 YL ESTER; BENZOIC ACID DERIVATIVE; CYCLOPENTA 2,4 DIENYL(4 METHOXYPHENYL)DIMETHYLSILANE; CYCLOPENTADIENE DERIVATIVE; FUMARIC ACID DIMETHYL ESTER; KETONE DERIVATIVE; PHOMOIDRIDE A; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; OXIDATION; PRECURSOR; PRIORITY JOURNAL; SILYLATION;

BETULACEAE;

EID: 1942504105     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.042     Document Type: Article

References (56)

1. Clive D.L.J., Sun S. Tetrahedron Lett. 42:2001;6267-6270.
2. Clive D.L.J., Ou L. Tetrahedron Lett. 43:2002;4559-4563.
3. Dabrah T.T., Kaneko T., Massefski W. Jr., Whipple E.B. J. Am. Chem. Soc. 119:1997;1594-1598.
4. Dabrah T.T., Harwood H.J. Jr., Huang L.H., Jankovich N.D., Kaneko T., Li J.-C., Lindsey S., Moshier P.M., Subashi T.A., Therrien M., Watts P.C. J. Antibiot. 50:1997;1-7.
5. Systematic numbering is used in the compound names given in Section 5, non-systematic numbering is used in Section 1.
6. Synthesis of 2:(a) Nicolaou K.C., Baran P.S., Zhong Y.-L., Choi H.-S., Yoon W.H., He Y., Fong K.C. Angew. Chem., Int. Ed. Engl. 38:1999;1669-1675.
7. Nicolaou K.C., Baran P.S., Zhong Y.-L., Fong K.C., He Y., Yoon W.H., Choi H.-S. Angew. Chem., Int. Ed. Engl. 38:1999;1676-1678.
8. Nicolaou K.C., Jung J.-K., Yoon W.H., He Y., Zhong Y.-L., Baran P.S. Angew. Chem., Int. Ed. Engl. 39:2000;1829-1832.
9. Nicolaou K.C., Zhong Y.-L., Baran P.S., Jung J., Choi H.-S., Yoon W.H. J. Am. Chem. Soc. 124:2002;2202-2211.
10. Tan Q., Danishefsky S.J. Angew. Chem., Int. Ed. Engl. 39:2000;4509-4511.
11. (f) Synthesis of the related CP-263,114: Parts a-e and g of this reference.
12. Waizumi N., Itoh T., Fukuyama T. J. Am. Chem. Soc. 122:2000;7825-7826.
13. Chen C., Layton M.E., Sheehan S.M., Shair M.D. J. Am. Chem. Soc. 122:2000;7424-7425.
14. Synthesis of naturally occurring isomers of CP-molecules: Meng D., Tan Q., Danishefsky S.J. Angew. Chem., Int. Ed. Engl. 38:1999;3197-3201.
15. For references to model studies, see Ref. 2, and (k) Bio M.M., Leighton J.L. J. Org. Chem. 68:2003;1693-1700.
16. Spiegel D.A., Njardarson J.T., Wood J.L. Tetrahedron. 58:2002;6545-6554.
17. Review: Spiegel D.A., Njardarson J.T., McDonald I.M., Wood J.L. Chem. Rev. 103:2003;2691-2727.
18. Fleming I., Michael J.P. J. Chem. Soc., Perkin Trans. 1. 1981;1549-1556.
19. Cf. (a) Allred E.L., Anderson C. J. Org. Chem. 32:1967;1874-1877.
20. Eaton P.E., Hudson R.A. J. Am. Chem. Soc. 87:1965;2769-2771.
21. Birney D.M., Berson J.A. Tetrahedron. 42:1986;1561-1570.
22. Cf. Saha G., Karpha A., Roy S.S., Ghosh S. J. Chem. Soc., Perkin Trans. 1. 1992;1587-1591.
23. Bis[(E)-5-heptenyl)copper lithium would be required for constructing the sidechain of CP-225,917.
24. For preparation of (E)-5-heptenoic acid, see: (a) Hudrlik P.F., Hudrlik A.M., Nagendrappa G., Yimenu T., Zeller E.T., Chin E. J. Am. Chem. Soc. 102:1980;6894-6896.
25. 4) (Ref. 11) and the resulting alcohol (Ref. 12) was converted into the mesylate (Ref. 13), and then into the bromide (Ref. 12).
26. Julia M., Maumy M. Bull. Soc. Chim. Fr. 1969;2415-2427.
27. Cf. Knight J.A., Diamond J.H. J. Org. Chem. 24:1959;400-403.
28. Tsai Y.-M., Chang F.-C., Huang J., Shiu C.-L., Kao C.-L., Liu J.-S. Tetrahedron. 53:1997;4291-4308.
29. It was expected that the Grignard reagent would be stable, and would not undergo cyclization: (a) Bailey W.F., Patricia J.J., DelGobbo V.C., Jarret R.M., Okarma P.J. J. Org. Chem. 50:1985;1999-2000. and references cited therein.
30. Cf. Sun P., Sun C., Weinreb S.M. J. Org. Chem. 67:2002;4337-4345.
31. Bartoli G., Bosco M., Pozzo R.D., Ciminale F. J. Org. Chem. 47:1982;5227-5229.
32. Jones G.R., Landais Y. Tetrahedron. 52:1996;7599-7662.
33. Toyama K., Iguchi S., Sakazaki H., Oishi T., Hirama M. Bull. Chem. Soc. Jpn. 74:2001;997-1008.
34. Yokoshima S., Tokuyama H., Fukuyama T. Angew. Chem., Int. Ed. 39:2000;4073-4075.
35. The atomic coordinates have been submitted to the Cambridge Crystallographic Data Centre.
36. Rieke R.D., Bales S.E. J. Am. Chem. Soc. 96:1974;1775-1781.
37. For preparation of several 5-silylated cyclopentadienes, see: Landais Y., Parrra-Rapado. Eur. J. Org. Chem. 2000;401-418.
38. Fleming I., Ghosh S.K. J. Chem. Soc., Chem. Commun. 1992;1775-1777.
39. Lee T.W., Corey E.J. Org. Lett. 3:2001;3337-3339.
40. Fleming I., Ghosh S.K. J. Chem. Soc. 1998;2711-2720.
41. Rahman A.N., Fleming I., Zwicky A.B. J. Chem. Soc. Miniprint. 1992;2401-2408.
42. Kolodyazhnyi Y.V., Gruntfest M.G., Dmitrieva V.K., Osipov O.A. J. Gen. Chem. USSR. 52:1982;554-558.
43. (c) Our chlorosilane was contaminated by a small amount of the corresponding bromosilane, as previously reported (this reference, part a).
44. For discussion of the fluxional behavior of 5-silylated cyclopentadienes, see: (a) Ashe A.J. III. J. Am. Chem. Soc. 92:1970;1233-1235.
45. Colvin E. Silicon in organic synthesis. 1981;Butterworths, London. Chapter 9, p 100.
46. Jutzi P. Chem. Rev. 86:1986;983-996.
47. Grimmond B.J., Corey J.Y. Organometallics. 18:1999;4646-4653.
48. Fleming I., Henning R., Plaut H. J. Chem. Soc., Chem. Commun. 1984;29-31.
49. Fleming I., Winter S.B.D. Tetrahedron Lett. 34:1993;7287-7290.
50. Rahman A.N., Fleming I. Synth. Commun. 23:1993;1583-1594.
51. Knölker H.-J., Wanzl G. Synlett. 1995;378-382.
52. 2O alone, see: Krohn K., Khanbabaee K. Liebigs Ann. Chem. 1994;1109-1112.
53. Crimmins M.T., Emmitte K.A., Choy A.L. Tetrahedron. 58:2002;1817-1834.
54. 3 (20.7 g) in water (150 mL). Flash chromatography silica gel (400 g) was poured in with vigorous swirling. Swirling was continued for 15 min after the addition and the solvents were removed under waterpump vacuum (rotary evaporator, bath temperature 40°C), the flask being protected from light with aluminum foil. The residual powder was kept under oil pump vacuum (protection from light) at 50°C for 12 h. The mixture was cooled and stored in a closed flask (protection from light). A sample of 4-hexen-1-ol (6.8 g) was chromatographed over this silica gel (5.5×29 cm), using 1:1 EtOAc-hexane (protection of the column from light), to obtain isomerically pure E-4-hexen-1-ol (5.9283 g) as a colorless oil. Two additional fractions (250 mg, mainly E-isomer) and (300 mg, mainly Z-isomer) were obtained. TLC plates for monitoring the chromatography were made by dipping a silica TLC plate into a sample of the above silver nitrate solution, and letting the plate air dry overnight in a cupboard.
55. 3 proceeded in poor yield (ca. 45%).
56. Clive D.L.J., Wickens P.L., Sgarbi P.W.M. J. Org. Chem. 61:1996;7426-7437.