FLUOROPROSTAGLANDINS - SYNTHESIS OF (+/-)-10-BETA-FLUOROPROSTAGLANDIN F2-ALPHA METHYL-ESTER

被引：25

作者：

GRIECO, PA

SUGAHARA, T

YOKOYAMA, Y

WILLIAMS, E

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 13期

关键词：

D O I：

10.1021/jo01327a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of 10γ-fluoroprostaglandin F2α methyl ester (1) is described. Treatment of the 10α,1lα-epoxyprostaglandin F2α methyl ester (24) with potassium bifluoride in hot ethylene glycol gave rise to (±)-l upon subsequent treatment with sodium hydroxide and reesterification. Epoxide 24 was synthesized from the known bicyclo[2.2.1]heptane derivative 10. Attempted preparation of (±)-l from the fluoro lactone 16 via the standard sequence [(a) reduction, (b) Wittig condensation, (c) CH22N22, and (d) cleavage of the tetrahydropyranyl ethers] gave none of the desired 10β-fluoroprostaglandin. A 70% yield of 9a, 10a-epoxyprostaglandin F2α methyl ester (17) was isolated. © 1979, American Chemical Society. All rights reserved.

引用

页码：2189 / 2193

页数：5

共 13 条

[1] ANDERSEN NH, 1969, J LIPID RES, V10, P316
[2] SYNTHESIS OF RING HALOGENATED PROSTAGLANDINS
ARRONIZ, CE
GALLINA, J
MARTINEZ, E
MUCHOWSKI, JM
VELARDE, E
[J]. PROSTAGLANDINS, 1978, 16 (01): : 47 - 65
[3] SHORT SYNTHESIS OF PROSTAGLANDINS FROM 5-CHLORO-5-CYANO-7-SYN-FORMYLBICYCLO[2,2,1]HEPT-2-ENE
BROWN, ED
LILLEY, TJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (02) : 39 - 39
[4] STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL)
COREY, EJ
WEINSHENKER, NM
SCHAAF, TK
HUBER, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) : 5675 - +
[5] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
[6] FRIED J, 1976, ADV PROSTAG THROMB R, V1, P183
[7] TOTAL SYNTHESIS OF 14-FLUOROPROSTAGLANDIN F2-ALPHA AND 14-FLUOROPROSTACYCLIN
GRIECO, PA
YOKOYAMA, Y
NICOLAOU, KC
BARNETTE, WE
SMITH, JB
OGLETREE, M
LEFER, AM
[J]. CHEMISTRY LETTERS, 1978, (09) : 1001 - 1004
[8] RING-FLUORINATED PROSTAGLANDINS - TOTAL SYNTHESIS OF (+/-)-10-ALPHA-FLUOROPROSTAGLANDIN F2-ALPHA METHYL-ESTER
GRIECO, PA
WILLIAMS, E
SUGAHARA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) : 2194 - 2199
[9] GRIECO PA, 1979, CHEM BIOCH PHARM ACT, P87
[10] 16-FLUORO-PROSTAGLANDINS
MAGERLEIN, BJ
MILLER, WL
[J]. PROSTAGLANDINS, 1975, 9 (04): : 527 - 530

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