Prostaglandin Endoperoxide Model Compounds. Part 1. Synthesis of (n + 5)-Bromodioxabicycloalkanes

DOI: 10.1039/P19810001375

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1375 - 1382 (1981)

Update date:2022-08-04

Topics:

Authors:

Bloodworth, A. J.

Eggelte, Henny J.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19810001375

Four cis-(n + 5)-bromodioxabicycloalkanes (12) (n= 2 - 5) have been prepared from C5-C8 cycloalkenes by the sequence singlet oxygenation, bromination, and treatment with silver trifluoroacetate.Photo-oxygenation of cycloalkenes provides a convenient route to the corresponding cycloalk-2-enyl hydroperoxides (6).Bromination of each of these proceeds smoothly in carbon tetrachloride to afford a mixture of cis-2,trans-3-dibromocycloalkyl hydroperoxide (10) and trans-2,cis-3-dibromocycloalkyl hydroperoxide (11).Except for 2,3-dibromocyclo-octyl hydroperoxide, the maior isomer obtained is (10) and the fraction of (10) in the mixture can be increased by silylating (6) with bistrimethylsilylacetamide before bromination and afterwards desilylating the dibromo-adducts by methanolysis.Both (10) and, less efficiently, (11) react with silver trifluoroacetate to give compounds (12), which are readily separated by low-temperature column chromatography from the bromo-trifluoroacetoxy-cycloalkyl hydroperoxides concurrently formed.Configurational assignments for (10), (11) and (12) have been made on the basis of spectroscopic date and chemical reactions.

Full text of DOI:10.1039/P19810001375

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:C₉H₁₈O₂Si

Cas No:72536-17-5

R&D Labs maybe for 72536-17-5

Luzhou North Chemical Co., Ltd.

Contact:+86-830-2796784；+86-830-2796776

Address:Gaoba, Longmatan District, Luzhou, Sichuan Province
Shanghai Xinda Pharmaceuticals Co., Ltd.

Contact:86-21-33692333-8008

Address:999 Linxian Road, Jinshan Industrial Park, Shanghai, China
Lyan Limited

Contact:86-021-52418058

Address:8/F, Building 6, Guiping Road No.333, Shanghai, 200233, China
Suzhou BEC Fine Chemicals Co., Ltd.

website:http://www.bek.com.cn

Contact:0512-68095917　 18913193865

Address:6, Jin Shan Road, Suzhou New District, 215011 China Suzhou Nations Pharmaceutical Innovation Center Inside
Hunan Haili Chemical Industry Co.,Ltd.

Contact:+86-731-85521860

Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China

Relevant to this article

Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase

Doi:10.1021/jm00378a028
(1984)
1,1-BIS(BENZENESULFONYL)ETHYLENE: A SYNTHETIC EQUIVALENT OF ETHYLENE 1,2-DIPOLE

Doi:10.1016/S0040-4039(01)91097-4
(1984)
Directed Ortho Metalation Induced Epoxy Cyclialkylation. Regiospecific 5-Exo-Tet and 6-Exo-Tet Routes to Benzofurans and Benzopyrans

Doi:10.1021/jo00199a061
(1984)
Doi:10.1021/jo01061a048
(1961)
Doi:10.1007/BF00637163
(1964)
Doi:10.1016/S0040-4020(01)99231-2
(1963)

Article Doi