TOTAL SYNTHESIS OF UPIAL, A MARINE SESQUITERPENE POSSESSING BICYCLO[3.3.1]NONANE RING-SYSTEM

被引：24

作者：

NAGAOKA, H

SHIBUYA, K

YAMADA, Y

机构：

[1] KOWA CO LTD,TOKYO RES LABS,HIGASHIMURAYAMA,TOKYO 189,JAPAN

[2] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)80785-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of marine sesquiterpene upial wets achieved starting from D-mannitol via sequential Michael reaction of the lithium enolate of 5 with methyl (E,S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-pentenoate((E)-6), fragmentation reaction of tricyclic compound 22 and samarium((li iodide-induced cyclization of diformate 3.

引用

收藏

页码：661 / 688

页数：28

相关论文

共 36 条

[1] AN UNEQUIVOCAL SYNTHESIS OF AN EXO-2-METHYLBICYCLO[3.3.1]NONAN-9-ONE [J].

BAKER, AJ ;

FRAZER, DV .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (05) :290-291

[2] LITHIUM CYANOHYDRIDOBORATE A VERSATILE NEW REAGENT [J].

BORCH, RF ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3996-&

[3]

Bulman P. C., 1991, COMPREHENSIVE ORGANI, V7, P83

[4] DIASTEREOFACIAL SELECTIVITY IN UNCATALYZED DIELS-ALDER CYCLOADDITIONS INVOLVING ALPHA, BETA-UNSATURATED ESTERS AND LACTONES WITH STEREOGENIC CENTERS CONTAINING OXYGEN FUNCTIONALITIES [J].

CASAS, R ;

PARELLA, T ;

BRANCHADELL, V ;

OLIVA, A ;

ORTUNO, RM ;

GUINGANT, A .

TETRAHEDRON, 1992, 48 (13) :2659-2680

[5]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[6] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[7]

GIBBONS GE, 1980, J ORG CHEM, V45, P1541

[8] PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].

GRIFFITH, WP ;

LEY, SV ;

WHITCOMBE, GP ;

WHITE, AD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627

[9] MICHAEL REACTIONS OF ALPHA-PHENYLTHIO AND ALPHA-PHENYLSULFINYL CROTONIC ESTERS WITH CYCLIC ENONES [J].

HAGIWARA, H ;

NAKAYAMA, K ;

UDA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (12) :3769-3770

[10] SODIUM PERBORATE - A MILD AND CONVENIENT REAGENT FOR EFFICIENTLY OXIDIZING TRIALKYLBORANES [J].

KABALKA, GW ;

SHOUP, TM ;

GOUDGAON, NM .

TETRAHEDRON LETTERS, 1989, 30 (12) :1483-1486

← 1 2 3 4 →