TOTAL SYNTHESIS OF PROSTAGLANDIN-E2 BY REARRANGEMENT OF A 6,8-DISUBSTITUTED-2-OXABICYCLO[3.2.1]OCTAN-3-ONE TO A 4,5-DISUBSTITUTED-PERHYDROCYCLOPENTA[B]FURAN-2-ONE

被引：17

作者：

NEWTON, RF ^{[1
]}

REYNOLDS, DP ^{[1
]}

WEBB, CF ^{[1
]}

YOUNG, SN ^{[1
]}

GRUDZINSKI, Z ^{[1
]}

ROBERTS, SM ^{[1
]}

机构：

[1] UNIV SALFORD,RAMAGE LABS,DEPT CHEM,SALFORD M5 4WT,LANCASHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 11期

关键词：

D O I：

10.1039/p19790002789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bis-silyloxylactone (5) has been converted into a prostaglandin-E 2 intermediate (7) using HCl or tetrabutylammonium fluoride.

引用

页码：2789 / 2792

页数：4

共 10 条

[1] ENANTIOMERIC PROSTAGLANDINS
COOPER, EL
YANKEE, EW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (18) : 5876 - 5894
[2] COOPER EL, 1974, J AM CHEM SOC, V96, P5884
[3] TOTAL SYNTHESIS OF PROSTAGLANDINS F1ALPHA, E1, F2ALPHA, AND E2 (NATURAL FORMS) FROM A COMMON SYNTHETIC INTERMEDIATE
COREY, EJ
NOYORI, R
SCHAAF, TK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) : 2586 - +
[4] IMPROVED SYNTHETIC ROUTES TO PROSTAGLANDINS UTILIZING SULFIDE-MEDIATED OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS
COREY, EJ
KIM, CU
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (06) : 1233 - 1234
[5] PHOTOSYNTHETIC ROUTES TO PROSTANOIDS - SYNTHESIS OF ALKYL AND TRIALKYLSILYL DERIVATIVES OF 9-ALPHA-HYDROXY-9-DEOXYPROSTAGLANDIN-C2
CROSSLAND, NM
ROBERTS, SM
NEWTON, RF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (23) : 886 - 887
[6] SYNTHESIS OF PROSTAGLANDIN-E2 AND PROSTAGLANDIN-C2 FROM 5-ENDO,7-ANTI-DISUBSTITUTED BICYCLO[2.2.1]HEPTAN-2-ONES
CROSSLAND, NM
ROBERTS, SM
NEWTON, RF
WEBB, CF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (15) : 660 - 661
[7] SYNTHESIS OF PROSTAGLANDIN-F-2-ALPHA BY CONJUGATE ADDITION OF A CUPRATE REAGENT TO 3-TERT-BUTYLDIMETHYLSILYLOXYTRICYCLO[3.2.0.02,7]HEPTAN-6-ONE
DIMSDALE, MJ
NEWTON, RF
RAINEY, DK
WEBB, CF
LEE, TV
ROBERTS, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (20) : 716 - 716
[8] DIMSDALE MJ, 1978, J CHEM SOC P1, P1176
[9] GRUDZINSKI Z, 1978, JCS P1, P1183
[10] HUNT BJ, 1967, CHEM IND-LONDON, P1868

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