Synthesis of the fully functionalized tris-oxazole fragment found in metabolites derived from marine organisms

被引：32

作者：

Liu, P ^{[1
]}

Celatka, CA ^{[1
]}

Panek, JS ^{[1
]}

机构：

[1] BOSTON UNIV,METCALF CTR SCI & ENGN,DEPT CHEM,BOSTON,MA 02215

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 31期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01218-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the fully functionalized tris-oxazole fragment 9 found in marine metabolites kabiramide C and halichondramide is reported employing modified Hantzsch methodology. Starting with the condensation reaction between cinnamamide 1 and ethyl bromopyruvate 2, the synthetic sequence leading to 9 was carried out in 13 steps with an overall yield of 26%. (C) 1997 Elsevier Science Ltd.

引用

页码：5445 / 5448

页数：4

共 12 条

[1] REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS [J].

AGUILAR, E ;

MEYERS, AI .

TETRAHEDRON LETTERS, 1994, 35 (16) :2473-2476

[2] MYCALOLIDES-A - C, HYBRID MACROLIDES OF ULAPUALIDES AND HALICHONDRAMIDE, FROM A SPONGE OF THE GENUS MYCALE [J].

FUSETANI, N ;

YASUMURO, K ;

MATSUNAGA, S ;

HASHIMOTO, K .

TETRAHEDRON LETTERS, 1989, 30 (21) :2809-2812

[3] MACROCYCLIC ANTIFUNGAL METABOLITES FROM THE SPANISH DANCER NUDIBRANCH HEXABRANCHUS-SANGUINEUS AND SPONGES OF THE GENUS HALICHONDRIA [J].

KERNAN, MR ;

MOLINSKI, TF ;

FAULKNER, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5014-5020

[4]

KNIGHT DW, 1990, SYNLETT, V1, P36

[5] BIOACTIVE MARINE METABOLITES .25. FURTHER KABIRAMIDES AND HALICHONDRAMIDES, CYTO-TOXIC MACROLIDES EMBRACING TRISOXAZOLE, FROM THE HEXABRANCHUS EGG MASSES [J].

MATSUNAGA, S ;

FUSETANI, N ;

HASHIMOTO, K ;

KOSEKI, K ;

NOMA, M ;

NOGUCHI, H ;

SANKAWA, U .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1360-1363

[6] KABIRAMIDE-C, A NOVEL ANTIFUNGAL MACROLIDE FROM NUDIBRANCH EGGMASSES .13. [J].

MATSUNAGA, S ;

FUSETANI, N ;

HASHIMOTO, K ;

KOSEKI, K ;

NOMA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :847-849

[7] TOTAL SYNTHESIS OF BIOACTIVE MARINE MACROLIDES [J].

NORCROSS, RD ;

PATERSON, I .

CHEMICAL REVIEWS, 1995, 95 (06) :2041-2114

[8] Studies directed toward the synthesis of ulapualide A. Asymmetric synthesis of the C8-C25 tris-oxazole fragment [J].

Panek, JS ;

Beresis, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6496-6497

[9] ULAPUALIDE-A AND ULAPUALIDE-B EXTRAORDINARY ANTITUMOR MACROLIDES FROM NUDIBRANCH EGGMASSES [J].

ROESENER, JA ;

SCHEUER, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :846-847

[10]

VANRHEENEN V, 1978, J ORG CHEM, V43, P2480

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