SEMIPREPARATIVE SYNTHESIS, C-13-NMR AND 2D-NMR OF PULOUPONE

被引：9

作者：

MATIKAINEN, J

KALTIA, S

HASE, T

KILPELAINEN, I

DRAKENBERG, T

ANNILA, A

机构：

[1] UNIV HELSINKI,DEPT CHEM,DIV ORGAN CHEM,VUORIKATU 20,SF-00100 HELSINKI 10,FINLAND

[2] UNIV HELSINKI,INST BIOTECHNOL,SF-00380 HELSINKI,FINLAND

[3] TECH RES CTR FINLAND,CHEM LAB,SF-02151 ESPOO,FINLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)88024-8

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：

A mmolar scale synthetic route to (+/-)-pulo'upone, in 9 steps, 3.8% overall yield, and under non-epimerizing conditions, is reported. A complete assignment of the compound's H-1 and C-13 NMR shifts is presented.

引用

页码：8007 / 8014

页数：8

共 17 条

[1]

STUDIES OF ENZYME-MEDIATED REACTIONS .10. STEREOCHEMICAL COURSE OF THE DEHYDROGENATION OF STEREOSPECIFICALLY LABELED 1-AMINO-HEPTANES BY THE AMINE OXIDASE FROM RAT-LIVER MITOCHONDRIA (EC 1434) [J].

BATTERSBY, AR ;

BUCKLEY, DG ;

STAUNTON, J ;

WILLIAMS, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2550-2558

[2]

NEW SYNTHESIS OF CYCLOHEXADIENE DERIVATIVES [J].

BOHLMANN, F ;

ZDERO, C .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (12) :3779-3787

[3]

TOTAL SYNTHESIS OF (+/-)-PULOUPONE [J].

BURKE, SD ;

PISCOPIO, AD ;

BUCHANAN, JL .

TETRAHEDRON LETTERS, 1988, 29 (23) :2757-2760

[4]

REAGENTS AND SYNTHETIC METHODS .64. PYRIDINE ASSISTED OXIDATIONS OF ALCOHOLS TO CARBONYL-COMPOUNDS BY MEANS OF 3-CARBOXYPYRIDINIUM DICHROMATE (NDC) REAGENT [J].

COSSIO, FP ;

LOPEZ, MC ;

PALOMO, C .

TETRAHEDRON, 1987, 43 (17) :3963-3974

[5]

AN INTRIGUING C-16-ALKADIENONE-SUBSTITUTED 2-PYRIDINE FROM A MARINE MOLLUSK [J].

COVAL, SJ ;

SCHEUER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3024-3025

[6]

Fouquet G., 1974, ANGEW CHEM, V86, P50

[7]

CYCLOPINOLENIC ACIDS - SYNTHESIS, DERIVATIVES AND THERMAL-PROPERTIES [J].

HASE, A ;

KALTIA, S ;

MATIKAINEN, J ;

ALAPEIJARI, M ;

HASE, T .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1992, 69 (10) :1027-1031

[8]

CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS [J].

KAGAN, HB ;

RIANT, O .

CHEMICAL REVIEWS, 1992, 92 (05) :1007-1019

[9]

KALTIA S, IN PRESS STEREOCHEMI

[10]

LEBIGOT Y, 1983, J AGR FOOD CHEM, P1096

← 1 2 →