Preparation of 14,36-didehydro pristinamycins IIs

Tetrahedron

Volumn 59, Issue 16, 2003, Pages 2929-2937

  Ronan, Baptiste ^a   Bacqué, Eric ^a   Barrière, Jean Claude ^a   Sablé, Serge ^a  

^a SANOFI   (France)

Author keywords

1,3 diketones; Acyl iminium; Allylic alcohols; Antibiotics; DDQ; Diels Alder reaction; Diols, enoxysilanes; DMP; Ketones; Oxidation; Pristinamycins II; Reduction; hydroxy ketones

Indexed keywords

14,36 DIDEHYDROPRISTANAMYCIN IIA; 14,36 DIDEHYDROPRISTANAMYCIN IIB; PRISTINAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DEGRADATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037437081     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00341-7     Document Type: Article

References (24)

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15. Dess-Martin Periodinane can be now purchased from Lancaster.
16. The 'crossover' experiments, reaction of 9 with DDQ and 10 with DMP, have not been done.
17. Diels-Alder reactions of DDQ across the dienic moiety of other PIIs have been already observed: Ronan, B.; Bacque, E.; Barrière, J. C. Unpublished results.
18. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
19. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
20. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
21. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
22. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
23. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.
24. For precedents of DDQ behaving as a dienophile in DA reactions, see: (a) Kuroda S., Oda M., Zuo S., Kanayama K., Shah S.I.M., Furuta S., Miyatake R., Kyogoku M. Tetrahedron Lett. 42:(36):2001;6345-6348 (b) Wallace Debra J., Gibb Andrew D., Cottrell Ian F., Kennedy Derek J., Brands Karel M.J., Dolling Ulf H. Synthesis. 2001;1784-1789 (c) Kasuhiro C., Takaaki A., Masahiro T. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (d) Takehiro S., Hoshie H., Hoshisuke T. Chem. Pharm. Bull. 38:(12):1990;3283-3295 (e) Nishida S., Murakami M., Oda H., Tsuji T., Mizuno T., Matsubara M., Kikai N. J. Org. Chem. 54:(16):1989;3859-3868 (f) Murakami M., Tsuji T., Oda H., Nishida S. Chem. Lett. 1987;863-866 (g) Rieger R., Breitmaier E. Synthesis. 1990;697-701.