Total synthesis of roseophilin

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2817-2825

  Fürstner, Alois ^a   Weintritt, Holger ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ROSEOPHILIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CELL VIABILITY; COUPLING FACTOR; CYTOTOXICITY; DRUG SYNTHESIS; NONHUMAN; SQUAMOUS CELL CARCINOMA; TARGET CELL;

EID: 0037644400     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973846k     Document Type: Article

References (67)

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9. For macrocyclization reactions via RCM from our laboratory, see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005-7008. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (e) Fürstner, A.; Müller, Th. Synlett 1997, 1010-1012. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, Ch. Angew. Chem. 1997, 109, 2562-2565. (h) Fürstner, A.; Müller, Th. J. Org. Chem. 1998, 63, 424-425.
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11. For macrocyclization reactions via RCM from our laboratory, see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 7005-7008. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746-8749. (e) Fürstner, A.; Müller, Th. Synlett 1997, 1010-1012. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130-9136. (g) Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, Ch. Angew. Chem. 1997, 109, 2562-2565. (h) Fürstner, A.; Müller, Th. J. Org. Chem. 1998, 63, 424-425.
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38. We did not investigate the structure of these dimers any further. However, there is some precedence in the literature that structurally related heterocyclic ketones are prone to dimerization, cf.: (a) Comer, M. C.; Despinoy, X. L. M.; Gould, R. O.; McNab, H.; Parsons, S. J. Chem. Soc. Chem. Commun. 1996, 1083-1084. (b) Neidlein, R.; Jeromin, G. Chem. Ber. 1982, 115, 706-713.
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46. Prepared according to: Bélanger, P. Tetrahedron Lett. 1979, 2505-2508.
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55. Fürstner, A.; Weintritt, H. Unpublished results.
56. The SEM group was chosen because it does not further increase the steric hindrance around the carbonyl group and it can be deprotected simultaneously with the TIPS substituent on the side chain by using fluoride. For a previous application of SEM-protected pyrroles, see: Edwards, M. P.; Doherty, A. M.; Ley, S. V.; Organ, H. M. Tetrahedron 1986, 42, 3723-3729.
57. The stereochemistry of the newly formed t-alcohol has not been rigorously assigned; the configuration shown in Scheme 11 is suggested by the inspection of molecular models.
58. The prodigiosin tripyrrole pigments are the closest relatives to roseophilin, cf.: (a) Wasserman, H. H.; Keith, D. D.; Nadelson, J. J. Am. Chem. Soc. 1969, 91, 1264-1265. (b) Laatsch, H.; Kellner, M.; Weyland, H. J. Antibiot. 1991, 44, 187-191. (c) Wasserman, H. H.; Keith, D. D.; Nadelson, J. Tetrahedron 1976, 32, 1867-1871. (d) Gerber, N.; N.; McInnes, A. G.; Smith, D. G.; Walter, J. A.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1978, 56, 1155-1163 and literature cited therein.
59. The prodigiosin tripyrrole pigments are the closest relatives to roseophilin, cf.: (a) Wasserman, H. H.; Keith, D. D.; Nadelson, J. J. Am. Chem. Soc. 1969, 91, 1264-1265. (b) Laatsch, H.; Kellner, M.; Weyland, H. J. Antibiot. 1991, 44, 187-191. (c) Wasserman, H. H.; Keith, D. D.; Nadelson, J. Tetrahedron 1976, 32, 1867-1871. (d) Gerber, N.; N.; McInnes, A. G.; Smith, D. G.; Walter, J. A.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1978, 56, 1155-1163 and literature cited therein.
60. The prodigiosin tripyrrole pigments are the closest relatives to roseophilin, cf.: (a) Wasserman, H. H.; Keith, D. D.; Nadelson, J. J. Am. Chem. Soc. 1969, 91, 1264-1265. (b) Laatsch, H.; Kellner, M.; Weyland, H. J. Antibiot. 1991, 44, 187-191. (c) Wasserman, H. H.; Keith, D. D.; Nadelson, J. Tetrahedron 1976, 32, 1867-1871. (d) Gerber, N.; N.; McInnes, A. G.; Smith, D. G.; Walter, J. A.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1978, 56, 1155-1163 and literature cited therein.
61. The prodigiosin tripyrrole pigments are the closest relatives to roseophilin, cf.: (a) Wasserman, H. H.; Keith, D. D.; Nadelson, J. J. Am. Chem. Soc. 1969, 91, 1264-1265. (b) Laatsch, H.; Kellner, M.; Weyland, H. J. Antibiot. 1991, 44, 187-191. (c) Wasserman, H. H.; Keith, D. D.; Nadelson, J. Tetrahedron 1976, 32, 1867-1871. (d) Gerber, N.; N.; McInnes, A. G.; Smith, D. G.; Walter, J. A.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1978, 56, 1155-1163 and literature cited therein.
62. Fürstner, A.; Krause, H.; Weintritt, H. Unpublished results.
63. For syntheses of other bioactive natural products from this laboratory see ref 4 and the following: (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641. (b) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786. (c) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (e) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336.
64. For syntheses of other bioactive natural products from this laboratory see ref 4 and the following: (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641. (b) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786. (c) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (e) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336.
65. For syntheses of other bioactive natural products from this laboratory see ref 4 and the following: (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641. (b) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786. (c) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (e) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336.
66. For syntheses of other bioactive natural products from this laboratory see ref 4 and the following: (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641. (b) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786. (c) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (e) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336.
67. For syntheses of other bioactive natural products from this laboratory see ref 4 and the following: (a) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641. (b) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773-786. (c) Fürstner, A.; Ernst, A.; Krause, H.; Ptock, A. Tetrahedron 1996, 52, 7329-7344. (d) Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078. (e) Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336.