Synthetic studies toward pyranonaphthoquinone antibiotics

被引：24

作者：

Brimble, MA ^{[1
]}

机构：

[1] Univ Auckland, Dept Chem, Auckland, New Zealand

来源：

PURE AND APPLIED CHEMISTRY | 2000年 / 72卷 / 09期

关键词：

D O I：

10.1351/pac200072091635

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A furofuran annulation/oxidative rearrangement strategy was used to construct the basic skeleton of the pyranonaphthoquinone family of antibiotics. This synthetic methodology has been applied to the synthesis of the spiroacetal-containing pyranonaphthoquinone antibiotic griseusin A, to an analog of the C-glycoside medermycin, and to a dimeric pyranonaphthoquinone.

引用

收藏

页码：1635 / 1639

页数：5

相关论文

共 12 条

[1]

Brimble M. A., 1996, MOLECULES, V1, P3, DOI [10.1007/S007830050002, DOI 10.1007/S007830050002]

[2] Synthetic strategies towards pyranonaphthoquinone antibiotics [J].

Brimble, MA ;

Nairn, MR ;

Prabaharan, H .

TETRAHEDRON, 2000, 56 (14) :1937-1992

[3] Synthesis of naphthyl C-glycosides of rearranged tri-O-benzyl-2-deoxy-D-glucose [J].

Brimble, MA ;

Brenstrum, TJ .

TETRAHEDRON LETTERS, 2000, 41 (07) :1107-1110

[4] Synthesis of a C-glycosylpyranonaphthoquinone related to medermycin [J].

Brimble, MA ;

Brenstrum, TJ .

TETRAHEDRON LETTERS, 2000, 41 (16) :2991-2994

[5] SYNTHESIS OF ARIZONIN C1 [J].

BRIMBLE, MA ;

PHYTHIAN, SJ ;

PRABAHARAN, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (22) :2855-2860

[6] SYNTHESIS OF 5-EPI-7-DEOXYKALAFUNGIN AND 5-EPI-7-O-METHYLKALAFUNGIN [J].

BRIMBLE, MA ;

STUART, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :881-885

[7] A SHORT SYNTHESIS OF DEOXYFRENOLICIN [J].

BRIMBLE, MA ;

LYNDS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :493-496

[8] Pyranonaphthoquinone antibiotics - isolation, structure and biological activity [J].

Brimble, MA ;

Duncalf, LJ ;

Nairn, MR .

NATURAL PRODUCT REPORTS, 1999, 16 (03) :267-281

[9] NATURALLY-OCCURRING QUINONES AS POTENTIAL BIOREDUCTIVE ALKYLATING-AGENTS [J].

MOORE, HW ;

CZERNIAK, R .

MEDICINAL RESEARCH REVIEWS, 1981, 1 (03) :249-280

[10] NEW ANTIBIOTIC, MEDERMYCIN [J].

TAKANO, S ;

HASUDA, K ;

ITO, A ;

KOIDE, Y ;

ISHII, F ;

HANEDA, I ;

CHIHARA, S ;

KOYAMA, Y .

JOURNAL OF ANTIBIOTICS, 1976, 29 (07) :765-768