STEREOCHEMISTRY AND TOTAL SYNTHESIS OF DOLASTATIN-E

被引:38
作者
NAKAMURA, M [1 ]
SHIBATA, T [1 ]
NAKANE, K [1 ]
NEMOTO, T [1 ]
OJIKA, M [1 ]
YAMADA, K [1 ]
机构
[1] NAGOYA UNIV, FAC SCI, DEPT CHEM, CHIKUSA KU, NAGOYA, AICHI 464, JAPAN
关键词
D O I
10.1016/0040-4039(95)00923-Z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of dolastatin E (1), a cyclic hexapeptide isolated from the sea hare Dolabella auricularia, has been determined by a combination of the degradation experiments and total synthesis.
引用
收藏
页码:5059 / 5062
页数:4
相关论文
共 29 条
[1]   REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS [J].
AGUILAR, E ;
MEYERS, AI .
TETRAHEDRON LETTERS, 1994, 35 (16) :2473-2476
[2]  
ALBIZATI KF, 1992, BIOORGANIC MARINE CH, V6, P24
[3]   TOTAL SYNTHESIS OF LISSOCLINAMIDE-5, A CYTOTOXIC CYCLIC PEPTIDE FROM THE TUNICATE LISSOCLINUM-PATELLA [J].
BODEN, C ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1994, 35 (44) :8271-8274
[4]   ASCIDIANS - PRODUCERS OF AMINO-ACID DERIVED METABOLITES [J].
DAVIDSON, BS .
CHEMICAL REVIEWS, 1993, 93 (05) :1771-1791
[5]   NOVEL CYTO-TOXIC COMPOUNDS FROM THE ASCIDIAN LISSOCLINUM-BISTRATUM [J].
DEGNAN, BM ;
HAWKINS, CJ ;
LAVIN, MF ;
MCCAFFREY, EJ ;
PARRY, DL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1354-1359
[6]   NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
DEGNAN, BM ;
HAWKINS, CJ ;
LAVIN, MF ;
MCCAFFREY, EJ ;
PARRY, DL ;
VANDENBRENK, AL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354
[7]   TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].
EVANS, DA ;
GAGE, JR ;
LEIGHTON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453
[8]   NICKEL PEROXIDE DEHYDROGENATION OF OXYGEN-CONTAINING, SULFUR-CONTAINING, AND NITROGEN-CONTAINING HETEROCYCLES [J].
EVANS, DL ;
MINSTER, DK ;
JORDIS, U ;
HECHT, SM ;
MAZZU, AL ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (04) :497-501
[9]   CONVENIENT RESOLUTION METHOD FOR PREPARATION OF ISOLEUCINE OPTICAL ISOMERS [J].
FLOURET, G ;
NAKAGAWA, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (18) :2635-2637
[10]   FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION [J].
GALEOTTI, N ;
MONTAGNE, C ;
PONCET, J ;
JOUIN, P .
TETRAHEDRON LETTERS, 1992, 33 (20) :2807-2810