First total synthesis of an exceptionally potent antitumor saponin, OSW-1

被引：139

作者：

Deng, SJ ^{[1
]}

Yu, B ^{[1
]}

Lou, Y ^{[1
]}

Hui, YZ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 01期

关键词：

D O I：

10.1021/jo981685c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

OSW-1 (1), an acylated disaccharide cholestane saponin from Ornithogalum saudersiae with exceptionally potent antitumor activity, was first synthesized from commercially available dehydroisoandrosterone, L-arabinose, and D-xylose in total 27 steps with the longest linear sequence of 14 steps and in 6% yield.

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页码：202 / 208

页数：7

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共 45 条

[21] First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.) [J].

Liu, MZ ;

Yu, B ;

Hui, YZ .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :415-418

[22] Total synthesis of tricolorin A [J].

Lu, SF ;

Oyang, QQ ;

Guo, ZW ;

Yu, B ;

Hui, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8400-8405

[23] STRUCTURE OF THE DIMETHYL SULFOXIDE OXALYL CHLORIDE REACTION-PRODUCT - OXIDATIONS OF HETEROAROMATIC AND DIVERSE ALCOHOLS TO CARBONYL-COMPOUNDS [J].

MANCUSO, AJ ;

BROWNFAIN, DS ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4148-4151

[24] A new rearranged cholestane glycoside from Ornithogalum saundersiae bulbs exhibiting potent cytostatic activities on leukemia HL-60 and MOLT-4 cells [J].

Mimaki, Y ;

Kuroda, M ;

Kameyama, A ;

Sashida, Y ;

Hirano, T ;

Oka, K ;

Dobashi, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) :2635-2638

[25] Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs [J].

Mimaki, Y ;

Kuroda, M ;

Kameyama, A ;

Sashida, Y ;

Hirano, T ;

Oka, K ;

Maekawa, R ;

Wada, T ;

Sugita, K ;

Beutler, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (05) :633-636

[26] SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .44. TOTAL SYNTHESIS OF SIALOSYLCEREBROSIDE, GM4 [J].

NUMATA, M ;

SUGIMOTO, M ;

KOIKE, K ;

OGAWA, T .

CARBOHYDRATE RESEARCH, 1987, 163 (02) :209-225

[27] HAWORTH MEMORIAL LECTURE - EXPERIMENTS DIRECTED TOWARDS GLYCOCONJUGATE SYNTHESIS [J].

OGAWA, T .

CHEMICAL SOCIETY REVIEWS, 1994, 23 (06) :397-&

[28] SYNTHESIS OF TETRASACCHARIDE AND TRISACCHARIDE SEQUENCES OF ASIALO-GMI AND ASIALO-GM2. REGIOSELECTIVE COUPLING OF THE GLYCOSIDATION OF LACTOSE [J].

PAULSEN, H ;

PAAL, M .

CARBOHYDRATE RESEARCH, 1985, 137 (MAR) :39-62

[29] ISOLATION AND STRUCTURE OF THE POWERFUL CELL-GROWTH INHIBITOR CEPHALOSTATIN-1 [J].

PETTIT, GR ;

INOUE, M ;

KAMANO, Y ;

HERALD, DL ;

ARM, C ;

DUFRESNE, C ;

CHRISTIE, ND ;

SCHMIDT, JM ;

DOUBEK, DL ;

KRUPA, TS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :2006-2007

[30] STEREOSPECIFIC SYNTHESIS OF (22R)-22-HYDROXYCHOLESTEROL AND (22R)-CHOLESTA-5,24-DIENE-3BETA,22-DIOL [J].

POYSER, JP ;

OURISSON, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (17) :2061-2066

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