Palladium-catalyzed cross-coupling of terminal alkynes with 4-trifloyloxazole: Studies toward the construction of the C26-C31 subunit of phorboxazole A

被引：60

作者：

Schaus, JV ^{[1
]}

Panek, JS ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 04期

关键词：

D O I：

10.1021/ol991306h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A strategy has been developed that successfully takes advantage of transition-metal-catalyzed coupling reactions for the synthesis of highly functionalized oxazoles. Trifloyloxazoles have been used as coupling partners with alkyne-derived vinylmetallic intermediates in Stille- and Negishi-type couplings to assemble the corresponding oxazoles in good isolated yield. The results obtained provide a close analogy and thus good precedent to employ this strategy in the synthesis of the oxazole subunits of phorboxazole A.

引用

页码：469 / 471

页数：3

共 18 条

[11]

RITTER K, 1993, SYNTHESIS-STUTTGART, P735

[12] PHORBOXAZOLE-A AND PHORBOXAZOLE-B - POTENT CYTOSTATIC MACROLIDES FROM MARINE SPONGE PHORBAS SP [J].

SEARLE, PA ;

MOLINSKI, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8126-8131

[13] Absolute configuration of phorboxazoles A and B from the marine sponge Phorbas sp .1. Macrolide and hemiketal rings [J].

Searle, PA ;

Molinski, TF ;

Brzezinski, LJ ;

Leahy, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9422-9423

[14]

TAYLOR RJK, 1994, ORGANOCOPPER REAGENT, P279

[15] A method for iodination of oxazoles at C-4 via 2-lithiooxazoles [J].

Vedejs, E ;

Luchetta, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1011-1014

[16] Studies on the total synthesis of the macrolide antitumor agent rhizoxin .2. Synthesis of the C14-C26 segment. [J].

White, JD ;

Holoboski, MA ;

Green, NJ .

TETRAHEDRON LETTERS, 1997, 38 (42) :7333-7336

[17]

WHITE JD, 1993, SYNLETT, P535

[18] SUBSTITUTED OXAZOLES - SYNTHESES VIA LITHIO INTERMEDIATES [J].

WHITNEY, SE ;

RICKBORN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :3058-3063

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