Biosynthesis of indole diterpenes, emindole, and paxilline: Involvement of a common intermediate

被引：28

作者：

Fueki, S ^{[1
]}

Tokiwano, T

Toshima, H

Oikawa, H

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

[2] Ibaraki Univ, Coll Agr, Dept Bioresource Sci, Tsukuba 3058642, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol049115o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The key step for construction of the carbon skeleton in the indole diterpenes, paxilline, and emindole DA was examined. Intact incorporation of multiply H-2-labeled 3-geranylgeranylindole into two different fungal metabolites proves 3-geranylgeranylindole to be a biosynthetic intermediate. These results give evidence that indole diterpenes are biosynthesized via epoxidation of a common intermediate, and the subsequent cationic cyclization, analogous to those in the steroid biosynthesis.

引用

页码：2697 / 2700

页数：4

共 26 条

[1]

ACKLIN W, 1977, CHIMIA, V31, P63

[2] PREPARATION AND REACTIONS OF 1-(TERT-BUTYLDIMETHYLSILYL)-3-LITHIOINDOLE, REGIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED INDOLES [J].

AMAT, M ;

HADIDA, S ;

SATHYANARAYANA, S ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :10-11

[3]

Betina V., 1989, MYCOTOXINS CHEM BIOL, V9

[4] Biosynthesis of nodulisporic acid A: Precursor studies [J].

Byrne, KM ;

Smith, SK ;

Ondeyka, JG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) :7055-7060

[5] Exploration of the biomimetic synthesis of indole-diterpene mycotoxins: an unexpected cascade reaction during the attempted synthesis of emindole SB [J].

Clark, JS ;

Myatt, J ;

Wilson, C ;

Roberts, L ;

Walshe, N .

CHEMICAL COMMUNICATIONS, 2003, (13) :1546-1547

[6] TREMORGENIC MYCO-TOXINS FROM PENICILLIUM-CRUSTOSUM - BIOSYNTHESIS OF PENITREM-A [J].

DE JESUS, AE ;

GORSTALLMAN, CP ;

STEYN, PS ;

VAN HEERDEN, FR ;

VLEGGAAR, R ;

WESSELS, PL ;

HULL, WE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1863-1868

[7] ANTIINSECTAN AFLAVININE DERIVATIVES FROM THE SCLEROTIA OF ASPERGILLUS-FLAVUS [J].

GLOER, JB ;

TEPASKE, MR ;

SIMA, JS ;

WICKLOW, DT ;

DOWD, PF .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5457-5460

[8] NOMININE - A NEW INSECTICIDAL INDOLE DITERPENE FROM THE SCLEROTIA OF ASPERGILLUS-NOMIUS [J].

GLOER, JB ;

RINDERKNECHT, BL ;

WICKLOW, DT ;

DOWD, PF .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2530-2532

[9] STRUCTURE OF A NEW-TYPE OF INDOLODITERPENOID FROM EMERICELLA-PURPUREA [J].

KAWAI, K ;

NOZAWA, K ;

NAKAJIMA, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (13) :1673-1674

[10] EMENIVEOL - A NEW POLLEN GROWTH INHIBITOR FROM THE FUNGUS, EMERICELLA-NIVEA [J].

KIMURA, Y ;

NISHIBE, M ;

NAKAJIMA, H ;

HAMASAKI, T ;

SHIGEMITSU, N ;

SUGAWARA, F ;

STOUT, TJ ;

CLARDY, J .

TETRAHEDRON LETTERS, 1992, 33 (46) :6987-6990

← 1 2 3 →