SELECTIVE REDUCTION OF SERRULATENOL AS A ROUTE TO SECO-PSEUDOPTEROSIN ANALOGS

被引：7

作者：

COWIN, LM ^{[1
]}

MASSYWESTROPP, RA ^{[1
]}

机构：

[1] UNIV ADELAIDE,DEPT ORGAN CHEM,GPO BOX 498,ADELAIDE,SA 5001,AUSTRALIA

来源：

JOURNAL OF NATURAL PRODUCTS | 1992年 / 55卷 / 12期

关键词：

D O I：

10.1021/np50090a015

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Deoxygenation of serrulatenol [3], from Eremophila rotundifolia, at C-13 and C-18, gave 5,8-dimethoxyserrulatane [12]. Catalytic hydrogenolysis and metal/NH3 cleavage of the allylic carbon-oxygen bond was followed by deoxygenation at C-18 via the tri-n-butylstannane reduction of the C-18 iodo derivative.

引用

页码：1790 / 1794

页数：5

共 9 条

[1] THE STRUCTURE OF A STABLE SERRULATANE DITERPENOID ACETAL FROM EREMOPHILA-ROTUNDIFOLIA [J].

ABELL, AD ;

HORN, E ;

JONES, GP ;

SNOW, MR ;

MASSYWESTROPP, RA ;

RICCIO, R .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (12) :1837-1845

[2] TOTAL SYNTHESIS OF (-)-PSEUDOPTEROSIN-A [J].

BROKA, CA ;

CHAN, S ;

PETERSON, B .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1584-1586

[3]

Harwood L. M., 1985, ALDRICHIM ACTA, V18, P25

[4]

KOZIKOWSKI AP, 1991, SYNLETT, P465

[5] THE PSEUDOPTEROSINS - ANTIINFLAMMATORY AND ANALGESIC NATURAL-PRODUCTS FROM THE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE [J].

LOOK, SA ;

FENICAL, W ;

JACOBS, RS ;

CLARDY, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (17) :6238-6240

[6] THE SECO-PSEUDOPTEROSINS, NEW ANTIINFLAMMATORY DITERPENE-GLYCOSIDES FROM A CARIBBEAN GORGONIAN OCTOCORAL OF THE GENUS PSEUDOPTEROGORGIA [J].

LOOK, SA ;

FENICAL, W .

TETRAHEDRON, 1987, 43 (15) :3363-3370

[7] THE PSEUDOPTEROSINS - A NEW CLASS OF ANTIINFLAMMATORY AND ANALGESIC DITERPENE PENTOSIDES FROM THE MARINE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE (OCTOCORALLIA) [J].

LOOK, SA ;

FENICAL, W ;

MATSUMOTO, GK ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5140-5145

[8] CONTROLLING BENZYLIC FUNCTIONALITY AND STEREOCHEMISTRY .1. SYNTHESIS OF THE SECOPSEUDOPTEROSIN AGLYCONE [J].

MCCOMBIE, SW ;

COX, B ;

LIN, SI ;

GANGULY, AK ;

MCPHAIL, AT .

TETRAHEDRON LETTERS, 1991, 32 (19) :2083-2086

[9]

UEMERA M, 1991, J AM CHEM SOC, V113, P5402

← 1 →