Synthesis of the C1′-C11′ oxazole-containing side chain of leucascandrolide A.: Application of a sonogashira cross-coupling

被引：53

作者：

Dakin, LA

Langille, NF

Panek, JS

机构：

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

[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Streamlined Synth, Boston, MA 02215 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 19期

关键词：

D O I：

10.1021/jo0204000

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, convergent synthesis of the C1'-C11' side chain (3) of leucascandrolide A (1) has been achieved. The key bond connection is made through the use of a palladium(0)-catalyzed Sonogashira cross-coupling between trifloyl oxazole (4) and alkynylmetal species (5).

引用

页码：6812 / 6815

页数：4

共 21 条

[1] [Anonymous], METAL CATALYZED CROS
[2] Campbell I. B., 1994, ORGANOCOPPER REAGENT, P217
[3] Synthesis of the C1-C13 fragment of leucascandrolide A
Crimmins, MT
Carroll, CA
King, BW
[J]. ORGANIC LETTERS, 2000, 2 (05) : 597 - 599
[4] D'Ambrosio M, 1999, HELV CHIM ACTA, V82, P347, DOI 10.1002/(SICI)1522-2675(19990310)82:3<347::AID-HLCA347>3.3.CO
[5] 2-0
[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[7] Leucascandrolide A, a new type of macrolide: The first powerfully bioactive metabolite of calcareous sponges (Leucascandra caveolata, a new genus from the coral sea)
DAmbrosio, M
Guerriero, A
Debitus, C
Pietra, F
[J]. HELVETICA CHIMICA ACTA, 1996, 79 (01) : 51 - 60
[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[9] HEGEDUS LS, 1994, ORGANOMETALLICS SYNT, P448
[10] Total synthesis of leucascandrolide A
Hornberger, KR
Hamblett, CL
Leighton, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12894 - 12895

← 1 2 3 →