Synthesis and cell cycle inhibition of the peptide enamide natural products terpeptin and the aspergillamides

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8931-8946

  Su, Shun ^a   Kakeya, Hideaki ^b   Osada, Hiroyuki ^b   Porco Jr , John A ^a  

^a Boston University   (United States)

^b Japan Science and Technology Agency   (Japan)

Author keywords

Aspergillamides; Cell cycle inhibitor; Indolic enamide; Oxidative decarboxylation elimination; Peptide; Terpeptin

Indexed keywords

ANTIMITOTIC AGENT; ASPERGILLAMIDE A; ASPERGILLAMIDE B; CELL CYCLE INHIBITOR; NATURAL PRODUCT; PEPTIDE DERIVATIVE; TERPETIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE INHIBITION; CONTROLLED STUDY; DECARBOXYLATION; DRUG ACTIVITY; DRUG SYNTHESIS; ELIMINATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0142186304     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.04.005     Document Type: Article

References (69)

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14. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
15. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
16. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
17. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
18. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
19. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
20. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
21. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
22. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
23. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
24. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
25. Chondriamides A and C: (a) Davyt D., Entz W., Fernandez R., Mariezcurrena R., Mombru A.W., Saldana J., Dominguez L., Coll J., Manta E. J. Nat. Prod. 61:1998;1560-1563. Terpeptin: (b) Kagamizono T., Sakai N., Arai K., Kobinata K., Osada H. Tetrahedron Lett. 38:1997;1223-1226. Aspergillamides: (c) Toske S.G., Jensen P.R., Kauffman C.A., Fenical W. Tetrahedron. 54:1998;13459-13466. Synthetic studies: (d) Beck B., Hess S., Domling A. Bioorg. Med. Chem. Lett. 10:2000;1701 (e) Rivas L., Quintero L., Fourrey J.-L., Benhida R. Tetrahedron Lett. 43:2002;7639-7641. (f) Coscinamide A: Bokesch H.R., Pannell L.K., McKee T.C., Boyd M.R. Tetrahedron Lett. 41:2000;6305-6308. (g) Synthetic studies: Kuramochi K., Osada Y., Kitahara T. Chem. Lett. 2:2002;128-129. Kottamide D: (h) Appleton D.R., Page M.J., Lambert G., Berridge M.V., Copp B.R. J. Org. Chem. 67:2002;5402-5404. (i) Frangufoline Gournelis D.C., Laskaris G.G., Verpoorte R. Cyclopeptide Alkaloids. Progress in the Chemistry of Organic Natural Products. 1998;1 Springer, New York. For additional indolic enamide natural products, see: fragilamide: (j) Kirkup M.P., Moore R.E. Tetrahedron Lett. 24:1983;2087-2090. Penidiamide (k) Witter L., Anke T., Sterner O. Z. Naturforsch., C: Biosci. 53:1998;60-64. Miyakamide: (l) Shiomi K., Hatae K., Yamaguchi Y., Masuma R., Tomoda H., Kobayashi S., Omura S. J. Antibiot. 55:2002;952-961.
26. For studies regarding the synthesis of indolic enamides, see Ref. 4h and: Brettle R., Mosedale A., J. J. Chem. Soc., Perkin Trans. 1. 8:1988;2185-2195.
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29. (a) Santanniello E., Farachi C., Ponti F. Synthesis. 8:1979;617-618. (b) For a review of sulfonamide protection of indoles, see: Ottoni O., Cruz R., Alves R. Tetrahedron. 54:1998;13915-13928.
30. (a) Santanniello E., Farachi C., Ponti F. Synthesis. 8:1979;617-618. (b) For a review of sulfonamide protection of indoles, see: Ottoni O., Cruz R., Alves R. Tetrahedron. 54:1998;13915-13928.
31. Use of a conventional TFA-based protocol led to reaction of the prenyl group to afford a trifluoroacetate adduct.
32. Commercially available from Argonaut Technologies (Foster City, CA) For a previous example of elimination (dehydrohalogenation) using PS-TBD resin, see: Tomoi M., Watanabe T., Suzuki T., Kakiuchi H. Makromol. Chem. 186:1985;2473-2481.
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35. For studies on spiroindolenine intermediates, see: (a) Nakagawa M., Liu J., Ogata K., Hino T. J. Chem. Soc., Chem. Commun. 1988;463-464 (b) Biswas K.M., Jackson A.H., Kobaisy M.M., Shannon P.V.R. J. Chem. Soc., Perkin Trans. 1. 4:1992;461-467.
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38. For effective coupling of N-methylated, sterically hindered amino acids using this reagent, see: (a) Angell Y.M., Garcia-Echeverria C., Rich D.H. Tetrahedron Lett. 35:1994;5981-5984. For a recent structural studies, see: (b) Carpino L.A., Imazumi H., El-Faham A., Ferrer F.J., Zhang C., Lee Y., Foxman B.M., Henklein P., Hanay C., Mugge C., Wenschuh H., Klose J., Beyermann M., Bienert M. Angew. Chem. Int. Ed. 41:2002;442-445.
39. For effective coupling of N-methylated, sterically hindered amino acids using this reagent, see: (a) Angell Y.M., Garcia-Echeverria C., Rich D.H. Tetrahedron Lett. 35:1994;5981-5984. For a recent structural studies, see: (b) Carpino L.A., Imazumi H., El-Faham A., Ferrer F.J., Zhang C., Lee Y., Foxman B.M., Henklein P., Hanay C., Mugge C., Wenschuh H., Klose J., Beyermann M., Bienert M. Angew. Chem. Int. Ed. 41:2002;442-445.
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41. 3 which cause degradation of sensitive functionality and inconsistencies in optical rotation measurements, see: Myers A.G., Siu M., Ren F. J. Am. Chem. Soc. 124:2002;4230-4232.
42. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
43. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
44. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
45. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
46. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
47. For recent reports regarding the synthesis of stereoisomers of natural products, see: (a) Fernandez R., Rodriguez J., Quinoa E., Riguera R., Munoz L., Fernandez-Suarez M., Debitus C. J. Am. Chem. Soc. 118:1996;11635-11643 (b) Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;4247-4251 (c) Berge J.M., Copley R.C.B., Eggleston D.S., Hamprecht D.W., Jarvest R.L., Mensah L.M., O'Hanlon P.J., Pope A.J. Biorg. Med. Chem. Lett. 10:2000;1811-1814 (d) Wipf P., Uto Y. J. Org. Chem. 65:2000;1037-1049 (e) Zhang Q., Rivkin A., Curran D.P. J. Am. Chem. Soc. 124:2002;5774-5781 (f) Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., Cook J.M. J. Med. Chem. 45:2002;1559-1562.
48. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
49. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
50. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
51. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
52. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
53. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
54. (a) Han H., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl Acad. Sci. USA. 92:1995;6419-6423 (b) Boger D.L., Tarby C.M., Myers P.L., Caporale L.H. J. Am. Chem. Soc. 118:1996;2109-2110 (c) Cheng S., Comer D.D., Williams J.P., Myers P.L., Boger D.L. J. Am. Chem. Soc. 118:1996;2567-2573. For recent reviews on parallel solution-phase synthesis using polymer reagents and scavengers, see: (d) Parlow J.J., Devraj R.V., South M.S. Curr. Opin. Chem. Biol. 3:1999;320-336 (e) Flynn D.L. Med. Res. Rev. 19:1999;408-431 (f) Brummer O., Clapham B., Janda K.D. Curr. Opin. Drug Discov. Dev. 3:2000;462-473 (g) Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., Taylor S.J. J. Chem. Soc., Perkin Trans. 1. 23:2000;3815-4195.
55. For scavenging of HOBt and coupling additives with amino-based scavenger resins, see: Weidner J.J., Parlow J.J., Flynn D.L. Tetrahedron Lett. 40:1999;239-242.
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57. Crystals of compound Nin-Ts-(12S,15R)-35 suitable for X-ray analysis were obtained by slow evaporation from EtOAc. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC # 208776). Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk).
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60. D=-113.7° (c=0.41, distilled MeOH), the optical rotation for natural 41 was not reported in Ref. 4c.
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