Practical synthesis of 7-prenylindole

被引：13

作者：

Xiong, Xin ^{[1
]}

Pirrung, Michael C. ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

D O I：

10.1021/jo070734v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

7-Prenylindole is a useful building block for natural product and natural product analogue synthesis. While there have been several past syntheses of 7-prenylindole, none of them is very practical for its preparation on scale. Using an aza-Claisen rearrangement as the key step, 7-prenylindole has been prepared in four steps from indoline in 62% overall yield.

引用

页码：5832 / 5834

页数：3

共 35 条

[1] CONSTITUENTS OF TROPICAL MEDICINAL-PLANTS .29. SYNTHESIS OF ANNONIDINE-B [J].

ACHENBACH, H ;

FRANKE, D .

ARCHIV DER PHARMAZIE, 1987, 320 (06) :574-576

[2] CONSTITUENTS OF TROPICAL MEDICINAL-PLANTS .24. SYNTHESES OF ANNONIDINE-A, ANNONIDINE-C AND ANNONIDINE-D [J].

ACHENBACH, H ;

FRANKE, D .

ARCHIV DER PHARMAZIE, 1987, 320 (01) :91-92

[3] INVESTIGATIONS ON WEST-AFRICAN MEDICINAL-PLANTS [J].

ACHENBACH, H .

PURE AND APPLIED CHEMISTRY, 1986, 58 (05) :653-662

[4] CONSTITUENTS OF WEST-AFRICAN MEDICINAL-PLANTS .18. THE ANNONIDINES - A NEW CLASS OF PRENYLATED BISINDOLE ALKALOIDS FROM ANNONIDIUM-MANNII [J].

ACHENBACH, H ;

RENNER, C .

HETEROCYCLES, 1985, 23 (08) :2075-2081

[5]

Agnaniet H., 2004, Journal of Essential Oil-Bearing Plants, V7, P201

[6]

ARAI K, 1981, CHEM PHARM BULL, V29, P1510

[7] ACID-CATALYZED [3,3]-SIGMATROPIC REARRANGEMENTS OF N-PROPARGYLANILINES [J].

BARMETTLER, P ;

HANSEN, HJ .

HELVETICA CHIMICA ACTA, 1990, 73 (06) :1515-1573

[8] PLANT SUBSTANCES .29. ISOLATION AND STRUCTURE OF 2 NEW INDOLE ALKALOIDS FROM RICCARDIA SINUATA (HOOK) TREV [J].

BENESOVA, V ;

SAMEK, Z ;

HEROUT, V ;

SORM, F .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1969, 34 (06) :1807-&

[9] PLANT SUBSTANCES .30. COMPONENTS OF LIVERWORTS (HEPATICAE) ANEURA PINGUIS (L) DUM, RICCARDIA SINUATA (HOOK) TREV, R INCURVATA LINDB AND CONOCEPHALUM CONICUM (L) UNDERW [J].

BENESOVA, V ;

HEROUT, V ;

SORM, F .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1969, 34 (06) :1810-&

[10] Composition of the leaf, stem bark and root bark oils of Isolona cooperi investigated by GC (retention index), GC-MS and 13C-NMR spectroscopy [J].

Boti, JB ;

Koukoua, G ;

N'Guessan, TY ;

Muselli, A ;

Bernardini, AF ;

Casanova, J .

PHYTOCHEMICAL ANALYSIS, 2005, 16 (05) :357-363

← 1 2 3 4 →