Total synthesis of eurypamides, marine cyclic-isodityrosines from the Palauan sponge Microciona eurypa

Tetrahedron

Volumn 60, Issue 26, 2004, Pages 5623-5634

  Ito, Miyuki ^a   Yamanaka, Maki ^a   Kutsumura, Noriki ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Eurypamides; Isodityrosine; L Threonine

Indexed keywords

2 (N BENZYLOXYCARBONYL)AMINO 2 DEOXY 3,4,5 TRIS(TERT BUTYLDIMETHYLSILYLOXY) 1 PIVALOYL DEXTRO ARABINITOL; 2 (N TERT BUTOXYCARBONYL)AMINO 2 DEOXY 3,4 BIS(TERT BUTYLDIMETHYLSILYLOXY) 1 PIVALOYL DEXTRO ARABINITOL; 2 (N TERT BUTOXYCARBONYL)AMINO 2 DEOXY 3,4,5 TRIS(TERT BUTYLDIMETHYLSILYLOXY) 1 PIVALOYL DEXTRO ARABINITOL; 4 (N TERT BUTOXYCARBONYL)AMINO 4 DEOXY 1 O TERT BUTYLDIMETHYLSILYL 5 O PIVALOYL DEXTRO RIBITOL; 4 (N TERT BUTOXYCARBONYL)AMINO 4 DEOXY 1,2,3 TRI O TERT BUTYLDIMETHYLSILYL DEXTRO RIBITOL; 4 (N TERT BUTOXYCARBONYL)AMINO 4 DEOXY 2,3,5 TRI O BENZYL 1 O TERT BUTYLDIMETHYLSILYL DEXTRO RIBITOL; 4 (TERT BUTOXYCARBONYL)AMINO 4 DEOXY 1,2,3 TRI O TERT BUTYLDIMETHYLSILYL 5 O PIVALOYL DEXTRO RIBITOL; 4 AZIDO 4 DEOXY 2,3,5 TRI O BENZYL 1 O TERT BUTYLDIMETHYLSILYL DEXTRO RIBITOL; ARABINITOL; ESTER DERIVATIVE; N TERT BUTOXYCARBONYL 2 O' DIIODOTYROSYLALLOTHREONYL 2 O' DIBROMOTYROSINE METHYL ESTER; N TERT BUTOXYCARBONYL 2 O' DIIODOTYROSYLTHREONYL 2 O' DIBROMOTYROSINE METHYL ESTER; N TERT BUTOXYCARBONYLALLOTHREONYL 2 O' DIBROMOTYROSINE METHYL ESTER; N TERT BUTOXYCARBONYLEURYPAMIDE B METHYL ESTER; N TERT BUTOXYCARBONYLEURYPAMIDE D METHYL ESTER; N TERT BUTOXYCARBONYLTHREONYL 2 O' DIBROMOTYROSINE METHYL ESTER; RIBITOL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; SPECTROSCOPY;

MICROCIONA; MICROCIONA EURYPA;

EID: 2942560506     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.062     Document Type: Article

References (9)

1. Yamamura S., Nishiyama S. Atta-ur-Rahman. Studies in Natural Products Chemistry. Vol. 10:1992;629-669 Elservier, Amsterdam
2. Yamamura S., Nishiyama S. J. Synth. Org. Chem. Jpn. 55:1997;1029-1039
3. An exception experienced was the case of K-13, in which the ether linkage was obtained, not at the iodine part but at the bromine position, probably owing to steric hindrance. See: Nishiyama S., Suzuki Y., Yamamura S. Tetrahedron Lett. 30:1989;379-382
4. Reddy M.V.R., Harper R.M., Faulkner D.J. Tetrahedron. 54:1998;10649-10656
5. Itokawa, H.; Watanabe, K.; Kawaoto, S.; Inoue, T. Jpn. Kokai Tokkyo Koho JP 63203671; Chem. Abstr. 110, 213362w.
6. Part of this investigation was preliminary reported Ito M., Yamanaka M., Kutsumura N., Nishiyama S. Tetrahedron Lett. 44:2003;7949-7952
7. Nishiyama S., Kim M.H., Yamamura S. Tetrahedron Lett. 35:1994;8397-8400
8. Yamamoto Y., Kirihata M., Ichimoto I., Ueda H. Agric. Biol. Chem. 49:1985;1435-1439
9. Naka T., Minakawa N., Abe H., Kaga D., Matsuda A. J. Am. Chem. Soc. 122:2000;7233-7243