Total synthesis of VM55599. Utilization of an intramolecular Diels-Alder cycloaddition of potential biogenetic relevance

被引：59

作者：

Stocking, EM ^{[1
]}

Sanz-Cervera, JF ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2000年 / 122卷 / 08期

关键词：

D O I：

10.1021/ja993791h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of VM55599, a natural metabolite of Penicillium sp. IMI332995, has been achieved via an intramolecular Diels-Alder cycloaddition of a reverse isoprene moiety across an azadiene system. The diastereoselectivity of the intramolecular Diels-Alder cycloaddition has biogenetic implications and is discussed in the context of the biogenetic relationship of VM55599 to the paraherquamides.

引用

页码：1675 / 1683

页数：9

共 75 条

[21]

DREYER DL, 1986, RECENT ADV PHYTOCHEM, V20, P317

[22] SYNTHETIC APPROACHES TO BREVIANAMIDE-A AND BREVIANAMIDE-B .1. PREPARATION OF 4-PARA-METHOXYBENZYL-5-(1'-CARBOMETHOXY-2'-[1'',1''-DIMETHYLALLYL-2',3'DIHYDROINDOLE]METHYLIDENE)-1,2-L-PYROLIDINOPIPERAZINE-3,6-DIONE VIA AN IRELAND ESTER ENOLATE CLAISEN REARRANGEMENT [J].

DUNKERTON, LV ;

CHEN, H ;

MCKILLICAN, BP .

TETRAHEDRON LETTERS, 1988, 29 (21) :2539-2542

[23] AN UNEXPECTED 1,3-DIPOLAR CYCLO-ADDITION OF 2-CHLOROACRYLONITRILE [J].

FABRE, JL ;

FARGE, D ;

JAMES, C ;

LAVE, D .

TETRAHEDRON LETTERS, 1985, 26 (44) :5447-5450

[24] (-)-Wistarin from the marine sponge Ircinia sp.:: the first case of enantiomeric sesterterpenes [J].

Fontana, A ;

Fakhr, I ;

Mollo, E ;

Cimino, G .

TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :3869-3872

[25] Stereocontrolled total synthesis of (+/-)-gelsemine [J].

Fukuyama, T ;

Liu, G .

PURE AND APPLIED CHEMISTRY, 1997, 69 (03) :501-505

[26]

Hano Y, 1999, HETEROCYCLES, V51, P231

[27]

HANO Y, 1989, CHEM PHARM BULL, V37, P554

[28]

HARRISON PHM, 1988, CHEMTRACTS ORG CHEM, V1, P369

[29] IRCINIANIN, A NOVEL SESTERTERPENE FROM A MARINE SPONGE [J].

HOFHEINZ, W ;

SCHONHOLZER, P .

HELVETICA CHIMICA ACTA, 1977, 60 (04) :1367-1370

[30]

ITO S, 1972, TETRAHEDRON LETT, P2557

← 1 2 3 4 5 6 7 8 →