Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata

被引：56

作者：

Murakami, N ^{[1
]}

Wang, WQ ^{[1
]}

Aoki, M ^{[1
]}

Tsutsui, Y ^{[1
]}

Higuchi, K ^{[1
]}

Aoki, S ^{[1
]}

Kobayashi, M ^{[1
]}

机构：

[1] OSAKA UNIV,FAC PHARMACEUT SCI,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(97)01194-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unidentified configurations at C-5 and C-10 in callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, were determined to be R, R by comparing the circular dichroism spectrum of 1 with those of two model compounds 2 and 3. Compounds 2 and 3 were synthesized by using E-selective Wittig olefination at the C-6-C-7 position as a key reaction. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：5533 / 5536

页数：4

相关论文

共 10 条

[1] MACROCYCLES BY OLEFINATION OF DIALDEHYDES WITH 1,3-BIS(DIMETHYLPHOSPHONO)-2-PROPANONE [J].

BUCHI, G ;

WUEST, H .

HELVETICA CHIMICA ACTA, 1979, 62 (08) :2661-2672

[2] LEPTOMYCIN-A AND LEPTOMYCIN-B NEW ANTI-FUNGAL ANTIBIOTICS .2. STRUCTURE ELUCIDATION [J].

HAMAMOTO, T ;

SETO, H ;

BEPPU, T .

JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :646-650

[3] ANGUINOMYCIN-C AND ANGUINOMYCIN-D, NEW ANTITUMOR ANTIBIOTICS WITH SELECTIVE CYTOTOXICITY AGAINST TRANSFORMED-CELLS [J].

HAYAKAWA, Y ;

SOHDA, K ;

SHINYA, K ;

HIDAKA, T ;

SETO, H .

JOURNAL OF ANTIBIOTICS, 1995, 48 (09) :954-961

[4] Studies on new antitumor antibiotics, leptofuranins A, B, C and D .2. Physicochemical properties and structure elucidation [J].

Hayakawa, Y ;

Sohda, KY ;

Seto, H .

JOURNAL OF ANTIBIOTICS, 1996, 49 (10) :980-984

[5] Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Kobayashi, M ;

Higuchi, K ;

Murakami, N ;

Tajima, H ;

Aoki, S .

TETRAHEDRON LETTERS, 1997, 38 (16) :2859-2862

[6]

KOBAYASHI M, 1995, CHEM PHARM BULL, V43, P1598

[7]

Kobayashi M, 1996, CHEM PHARM BULL, V44, P2142

[8] STRUCTURAL STUDY OF A NEW ANTITUMOR ANTIBIOTIC, KAZUSAMYCIN [J].

KOMIYAMA, K ;

OKADA, K ;

OKA, H ;

TOMISAKA, S ;

MIYANO, T ;

FUNAYAMA, S ;

UMEZAWA, I .

JOURNAL OF ANTIBIOTICS, 1985, 38 (02) :220-223

[9] DIRECT SYNTHESIS OF Z-UNSATURATED ESTERS - A USEFUL MODIFICATION OF THE HORNER-EMMONS OLEFINATION [J].

STILL, WC ;

GENNARI, C .

TETRAHEDRON LETTERS, 1983, 24 (41) :4405-4408

[10] STEREOSELECTIVE-E AND STEREOSELECTIVE-Z OLEFIN FORMATION BY WITTIG OLEFINATION OF ALDEHYDES WITH ALLYLIC PHOSPHORUS YLIDES - STEREOCHEMISTRY [J].

TAMURA, R ;

SAEGUSA, K ;

KAKIHANA, M ;

ODA, D .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2723-2728