Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Organocuprate conjugate-addition–enolate-alkylation reactions: a new synthesis of 11-deoxyprostaglandins

Andrew J. Dixon,   Richard J. K. Taylor  and  Roger F. Newton  

Abstract

A short synthesis of a key 11-deoxyprostaglandin precursor, 6β-[(E)-3-oxo-oct-1-enyl]-cis-α-2-oxabicyclo-[3.3.0]octan-3-one (11), is reported. Important reactions in the synthesis include preparation of 2α-allyl-3β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}cyclopentanone (4) by an organocuprate conjugate-addition–enolate-alkylation reaction, regiospecific epoxidation–cyclisation of the alcohol (7) to give 6β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}-3-hydroxymethyl-cis-α-2-oxabicyclo[3.3.0]octane (9), and oxidative degradation of (9) with manganese dioxide to give 6β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}-cis-α-2-oxabicyclo-[3.3.0]octan-3-one (10).

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P19810001407
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1407-1410

Permissions

Request permissions

Organocuprate conjugate-addition–enolate-alkylation reactions: a new synthesis of 11-deoxyprostaglandins

A. J. Dixon, R. J. K. Taylor and R. F. Newton, J. Chem. Soc., Perkin Trans. 1, 1981, 1407 DOI: 10.1039/P19810001407

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements