Stereoselective synthesis of CD-ring precursors of vitamin D derivatives

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 7001-7015

  Rodriguez, Raphaël ^a   Chapelon, Anne Sophie ^a   Ollivier, Cyril ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLOXAZABOROLIDIN DERIVATIVE; ACETYLMETHYLDIVINYLCYCLOPENTANE; BORANE DERIVATIVE; BORON; BORON DERIVATIVE; CYCLOPENTANE DERIVATIVE; EPOXYKETONE; HYDRINDANE DERIVATIVE; IMINE; INDAN DERIVATIVE; KETONE; O ETHYL (S OCTAHYDRO 7A METHYL 7 OXO 1 VINYL 1H INDEN 4 YL)CARBONODITHIOATE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION KINETICS; CIRCULAR DICHROISM; CYCLIZATION; DESS MARTIN OXIDATION; DRUG PURITY; EPOXIDATION; MOLECULAR MODEL; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REDUCTION KINETICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 67650538334     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.052     Document Type: Article

References (103)

1. In: Feldman D., Glorieux F.H., and Pike J.W. (Eds). Vitamin D (1997), Academic, New York, NY
2. In: Norman A.W., Bouillon R., and Thomasset M. (Eds). Vitamin D Endocrine System: Structural, Biological, Genetic and Clinical Aspects (2000), University of California Riverside, Riverside, CA
3. Bouillon R., Okamura W.H., and Norman A.W. Endocr. Rev. 16 (1995) 200-257
4. For reviews on this topic, see:
5. Dai H., and Posner G.H. Synthesis (1994) 1383-1398
6. Zhu G.-D., and Okamura W.H. Chem. Rev. 95 (1995) 1877-1952
7. Posner G.H., and Kahraman M. Eur. J. Org. Chem. (2003) 3889-3895
8. Chapelon A.S., Moraleda D., Rodriguez R., Ollivier C., and Santelli M. Tetrahedron 63 (2007) 11511-11616
9. Kabat M.M., and Radinov R. Curr. Opin. Drug Discov. Dev. 4 (2001) 808-833
10. Okamura W.H., Zhu G.-D., Hill D.K., Thomas R.J., Ringe K., Borchardt D.B., Norman A.W., and Mueller L.J. J. Org. Chem. 67 (2002) 1637-1650 and reference therein
11. For a review, see:. Jankowski P., Marczak S., and Wicha J. Tetrahedron 54 (1998) 12071-12150
12. Steroidal numbering is used.
13. Baggiolini E.G., Iacobelli J.A., Hennessy B.M., and Uskoković M.R. J. Am. Chem. Soc. 104 (1982) 2945-2948
14. Nemoto H., Kurobe H., Fukumoto K., and Kametani T. J. Org. Chem. 51 (1986) 5311-5320
15. Daniewski A.R., and Kiegiel J. J. Org. Chem. 53 (1988) 5534-5535
16. Fernàndez B., Martinez Pérez J.A., Granja J.R., Castedo L., and Mouriño A. J. Org. Chem. 57 (1992) 3173-3178
17. Jankowski P., Marczak S., and Wicha J. Tetrahedron 54 (1998) 12071-12150
18. Daniewski A.R., and Liu W. J. Org. Chem. 66 (2001) 626-628
19. Chochrek P., and Wicha J. Org. Lett. 8 (2006) 2551-2553
20. Chochrek P., Kurek-Tyrlik A., Michalak K., and Wicha J. Tetrahedron Lett. 47 (2006) 6017-6020
21. Pardo R., Archier P., and Santelli M. Bull. Soc. Chim. Fr. (1986) 760-765
22. Gordon H.L., Freeman S., and Hudlicky T. Synlett (2005) 2911-2914 and references therein
23. Allinger N.L., and Tribble M.T. Tetrahedron 28 (1972) 1191-1202
24. Lo Cicero B., Weisbuch F., and Dana G. J. Org. Chem. 46 (1981) 914-919
25. Quinkert G. Experientia 13 (1957) 381-389
26. Inhoffen H.H., Quinkert G., Schutz S., Kampe D., and Domagk G.F. Chem. Ber. 90 (1957) 664-673
27. Pellissier H., Toupet L., and Santelli M. J. Org. Chem. 59 (1994) 1709-1713
28. Mariet N., Pellissier H., Ibrahim-Ouali M., and Santelli M. Eur. J. Org. Chem. (2004) 2679-2691
29. Rodriguez R., Ollivier C., and Santelli M. Tetrahedron Lett. 44 (2004) 2289-2292
30. trans-Hydrindanone precursors of CD-ring system of vitamin D have previously been obtained from meso-3, for premilary communications see:
31. Rodriguez R., Ollivier C., and Santelli M. Synlett (2006) 312-314
32. Chapelon A.-S., Ollivier C., and Santelli M. Tetrahedron Lett. 47 (2006) 2747-2750
33. For reviews, see:
34. Hoveyda A.H., Evans D.A., and Fu G.C. Chem. Rev. 93 (1993) 1307-1370
35. Hartung J., and Greb M. J. Organomet. Chem. 661 (2002) 67-84
36. Mitome H., Miyaoka H., and Yamada Y. Tetrahedron Lett. 41 (2000) 8107-8110
37. 12 position increased to 4.4 times the affinity of the related calcitriol analogs for the vitamin D receptor (VDR). Gonzalès-Avión X.C., and Mouriño A. Org. Lett. 5 (2003) 2291-2293
38. First, we considered a ketone-directed epoxidation of anti meso-3. Attempts performed with meta-chloroperbenzoic acid at rt led to a 50:50 mixture of two monoepoxides diastereoisomers, resulting from a total lack of facial selectivity.
39. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155-4156
40. Sabitha G., Satheesh Babu R., Rajkumar M., Srinivas Reddy Ch., and Yadav J.S. Tetrahedron Lett. 42 (2001) 3955-3958
41. Bartoli G., Marcantoni E., and Sambri L. Synlett (2003) 2101-2116
42. N2 cycloalkylation of the corresponding seco-iodo compound, see:. Okamura W.H., Zhu G.-D., Hill D.K., Thomas R.J., Ringe K., Borchardt D.B., Norman A.W., and Mueller L.J. J. Org. Chem. 67 (2002) 1637-1650
43. For a review, see:. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986-2012
44. Separation of both diastereoisomers at the previous stage should provided a better er. Unfortunatly, attemps to remove the minor stereoisomer by flash chromatography were unfruitful. Efforts to solve this problem are still under studies.
45. The enatiomeric ratio (er) was calculated from the chiral GC values of (+)-4, 8a and 8 as detailed in experimental section.
46. Kocienski P.J., Lythgoe B., and Ruston S. J. Chem. Soc., Perkin Trans. 1 (1979) 1290-1293
47. Blakemore P.R., Grzywacz P., Kocienski P.J., Marczak S., and Wicha J. Pol. J. Chem. 73 (1999) 1209-1217
48. Blakemore P.R., Kocienski P.J., Marczak S., and Wicha J. Synthesis (1999) 1209-1215
49. Plesniak K., Zarecki A., and Wicha J. Top. Curr. Chem. 275 (2007) 163-250
50. Kocienski P.J. Chem. Ind. (1981) 548-551
51. Kocienski P.J. Phosphorus Sulfur Silicon Relat. Elem. 24 (1985) 477-507
52. Blakemore P.R., Cole W.J., Kocienski P.J., and Morley A. Synlett (1998) 26-28
53. Kocienski P.J., Bell A., and Blakemore P.R. Synlett (2000) 365-366
54. Julia M., and Paris J.-M. Tetrahedron Lett. (1973) 4833-4836
55. For reviews on the chemistry of xanthates, see:
56. Quiclet-Sire B., and Zard S.Z. Chem.-Eur. J. 12 (2006) 6002-6016
57. Quiclet-Sire B., and Zard S.Z. Top. Curr. Chem. 264 (2006) 201-236
58. Zard S.Z. Angew. Chem., Int. Ed. 36 (1997) 672-685
59. Quiclet-Sire B., and Zard S.Z. Phosphorus, Sulfur Silicon Relat. Elem. 153-154 (1999) 137-145
60. Zard S.Z. In: Renaud P., and Sibi M. (Eds). Radical in Organic Synthesis. 1st ed. (2001), Wiley-VCH GmbH, Weinheim, Germany 90
61. For examples of cyclization of an α-carbonyl radical generated from the corresponding xanthate, see:
62. Bacqué E., Pautrat F., and Zard S.Z. Org. Lett. 5 (2003) 325-328
63. Briggs M.E., El Qacemi M., Kalaï C., and Zard S.Z. Tetrahedron Lett. 45 (2004) 6017-6020
64. Pellissier H., and Santelli M. Tetrahedron 52 (1996) 9093-9100
65. Ester and malonate xanthate derivatives have been reported to be synthetized by reaction of their respective enolates with diethyl bisdithiocarbonate in 50-58% yield.
66. Maslak V., Čeković Z., and Saičić R.N. Synlett (1998) 1435-1437
67. Shi L., Chapman T.M., and Beckman E.J. Macromolecules 36 (2003) 2563-2567
68. Julia M. Acc. Chem. Res. 4 (1971) 386-392
69. For a review on acyl radicals see:. Chatgilialoglu C., Crich D., Komatsu M., and Ryu I. Chem. Rev. 99 (1999) 1991-2070
70. Clive D.L.J., and Cheshire D.R. J. Chem. Soc., Chem. Commun. (1987) 1520-1523
71. Porter N.A., Chang V.H.-T., Magnin D.R., and Wright B.T. J. Am. Chem. Soc. 110 (1988) 3554-3560
72. Curran D.P., and Chang C.-T. J. Org. Chem. 54 (1989) 3140-3157
73. Broeker J.L., and Houk K.N. J. Org. Chem. 56 (1991) 3651-3655
74. *, see:. Chatgilialoglu C., Ferreri C., Guerra M., Timokhin V., Froudakis G., and Gimisis T. J. Am. Chem. Soc 124 (2002) 10765-10772
75. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D.02 (2003), Gaussian, Pittsburgh, PA
76. Bruice T.C., and Lightstone F.C. J. Am. Chem. Soc. 118 (1996) 2595-2605
77. Repasky M.P., Guimarães C.R.W., Chandrasekhar J., Tirado-Rives J., and Jorgensen W.L. J. Am. Chem. Soc. 125 (2003) 6663-6672
78. Pintér B., De Proft F., Van Speybroeck V., Hemelsoet K., Waroquier M., Chamorro E., Veszprémi T., and Geerlings P. J. Org. Chem. 72 (2007) 348-356
79. Menger F.M. Acc. Chem. Res. 18 (1985) 128-134
80. Bürgi H.B., and Dunitz J.D. Acc. Chem. Res. 16 (1983) 153-161
81. Bauschlicher Jr. C.W., and Partridge H. J. Chem. Phys. 103 (1995) 1788-1791
82. Mori K., and Nakamura Y. J. Org. Chem. 34 (1969) 4170-4172
83. Boivin J., Ramos L., and Zard S.Z. Tetrahedron Lett. 39 (1998) 6877-6880
84. Boivin J., Pothier J., Ramos L., and Zard S.Z. Tetrahedron Lett. 40 (1999) 9239-9241
85. Chen C.H. J. Heterocycl. Chem. 13 (1976) 1079-1084
86. Martel S., and Prandi J. J. Chem. Soc., Perkin Trans. 1 (2001) 305-315
87. Cane D.E., Yang G., Coates R.M., Pyun H.J., and Hohn T.M. J. Org. Chem. 57 (1992) 3454-3462
88. Srikrishna A., and Kumar P.P. Tetrahedron 56 (2000) 8189-8195
89. He A., Yan B., Thanavaro A., Spilling C.D., and Rath N.P. J. Org. Chem. 69 (2004) 8643-8651
90. Taylor R.E., Engelhardt F.C., Schmitt M.J., and Yaun H. J. Am. Chem. Soc. 123 (2001) 2964-2969
91. Calvet G., Blanchard N., and Kouklovsky C. Org. Lett. 9 (2007) 1485-1488
92. Matsui S. Bull. Chem. Soc. Jpn. 60 (1987) 1853-1865
93. Carrea A., Denis J.N., and Greene A.E. Synth. Commun. 21 (1991) 1-9
94. Chiacchio U., Corsaro A., Rescifina A., Bkaithan M., Grassi G., Piperno A., Privitera T., and Romeo G. Tetrahedron 57 (2001) 3425-3433
95. Johnson C.R., and Zeller J.R. J. Am. Chem. Soc. 104 (1982) 4021-4023
96. Johnson C.R., and Zeller J.R. Tetrahedron 40 (1984) 1225-1233
97. Brandt J., and Gais H.-J. Tetrahedron: Asymmetry 8 (1997) 909-912
98. Shiner C.S., and Berks A.J. J. Org. Chem. 53 (1988) 5542-5545
99. Kraehenbuehl K., Picasso S., and Vogel P. Helv. Chim. Acta 81 (1998) 1439-1479
100. Weber J.V., Schneider M., Salami B., and Paquer D. Recl. Trav. Chim. Pays-Bas 105 (1986) 99-102
101. Johnson C.R., Haake M., and Schroeck C.W. J. Am. Chem. Soc. 92 (1970) 6594-6598
102. Johnson C.R., and Schroeck C.W. J. Am. Chem. Soc. 95 (1973) 7418-7423
103. Boga C., Del Vecchio E., Forlani L., and Todesco P.E. J. Organomet. Chem. 601 (2000) 233-236