Synthesis of gibberellin GA(53) and its (17,17-D-2)derivative

被引：10

作者：

Mander, LN

Owen, DJ

Twitchin, B

机构：

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1996年 / 49卷 / 02期

关键词：

D O I：

10.1071/CH9960249

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gibberellin GA(53) (1) has been prepared by a modified Wolff-Kishner reduction of gibberellin GA(19) protected as its 13-methoxymethyl ether (11). Careful regulation of the temperature at c. 174 degrees is necessary, otherwise migration of the 16-ene function into the endocyclic 15-ene position occurs to an increasing extent at higher temperatures. The methodology was also extended to the preparation of the (17,17-D-2)derivative (20).

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页码：249 / 253

页数：5

相关论文

共 19 条

[1]

BARTLETT PA, 1970, TETRAHEDRON LETT, P4459

[2]

BARTON DHR, 1955, J CHEM SOC, P2056

[3] CONJUGATE ADDITION OF LITHIUM METHYLCUPRATES TO A GIBBERELL-1(10)EN-2-ONE - PREPARATION OF 10-EPI-GIBBERELLIN A53 [J].

BEALE, MH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (06) :1147-1150

[4] FUNGAL PRODUCTS .15. METABOLISM OF STEVIOL TO 13-HYDROXYLATED ENT-GIBBERELLANES AND ENT-KAURANES [J].

BEARDER, JR ;

MACMILLAN, J ;

WELS, CM ;

PHINNEY, BO .

PHYTOCHEMISTRY, 1975, 14 (08) :1741-1748

[5] BIOSYNTHESIS OF GIBBERELLINS .3. [J].

CROSS, BE ;

NORTON, K ;

STEWART, JC .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09) :1054-&

[6] STEREOCONTROLLED SYNTHESIS OF GIBBERELLIN-A19 FROM GIBBERELLIC-ACID [J].

DAWE, RD ;

MANDER, LN ;

TURNER, JV .

TETRAHEDRON LETTERS, 1985, 26 (03) :363-366

[7] SYNTHESES OF C-20 GIBBERELLIN-A36 AND GIBBERELLIN-A37 METHYL-ESTERS FROM GIBBERELLIC-ACID [J].

DAWE, RD ;

MANDER, LN ;

TURNER, JV ;

PAN, XF .

TETRAHEDRON LETTERS, 1985, 26 (46) :5725-5728

[8] PREPARATION OF 13-HYDROXYGIBBERELLIN A12-7-ALDEHYDE [J].

DOWN, GJ ;

LEE, M ;

MACMILLAN, J ;

STAPLES, KS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (05) :1103-1108

[9] NEW METABOLITES OF GIBBERELLA FUJIKUROI .7. PREPARATION OF SOME RING-B NOR-DERIVATIVES [J].

GALT, RHB .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1565-&

[10]

HUANGMINLON, 1949, J AM CHEM SOC, V71, P2487