Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: utility of solid state Baeyer-Villiger oxidation

被引：23

作者：

Hagiwara, H

Nagatomo, H

Kazayama, S

Sakai, H

Hoshi, T

Suzuki, T

Ando, M

机构：

[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan

[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 04期

关键词：

D O I：

10.1039/a808964g

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Norsesquiterpenoid 1 has been synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 3 via solid state Baeyer-Villiger oxidation as a key step.

引用

页码：457 / 459

页数：3

共 8 条

[1]

NEW AND SELECTIVE REACTIONS AND REAGENTS IN CARBOHYDRATE-CHEMISTRY [J].

BARTON, DHR ;

MOTHERWELL, WB .

PURE AND APPLIED CHEMISTRY, 1981, 53 (01) :15-31

[2]

Demnitz FWJ, 1996, SYNTHESIS-STUTTGART, P1305

[3]

OPTICALLY PURE (4AS)-(+)- OR (4AR)-(-)-1,4A-DIMETHYL-4,4A,7,8-TETRAHYDRONAPHTHALENE-2,5(3H,6H)-DIONE AND ITS USE IN THE SYNTHESIS OF AN INHIBITOR OF STEROID-BIOSYNTHESIS [J].

HAGIWARA, H ;

UDA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2308-2311

[4]

Hashimoto T, 1998, HETEROCYCLES, V47, P1067

[5]

KOTSUKI H, 1998, 74 ANN M CHEM SOC JA, P746

[6]

NEW CHIRAL ANISOTROPIC REAGENTS FOR DETERMINING THE ABSOLUTE-CONFIGURATION OF CARBOXYLIC-ACIDS [J].

NAGAI, Y ;

KUSUMI, T .

TETRAHEDRON LETTERS, 1995, 36 (11) :1853-1856

[7]

AN EFFICIENT APPROACH TO CHIRAL, NONRACEMIC TRANS-DECAHYDRO-5,8A-DIMETHYL-1,6-NAPHTHALENEDIONE DERIVATIVES - TOTAL SYNTHESIS OF (+)-PALLESCENSIN-A [J].

SMITH, AB ;

MEWSHAW, R .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3685-3689

[8]

BAEYER-VILLIGER REACTION IN THE SOLID-STATE [J].

TODA, F ;

YAGI, M ;

KIYOSHIGE, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) :958-959

← 1 →