Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 24
98
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

A Novel Chemo‐selective Epoxidation across Acrylate Ester: Synthesis of New Water‐Soluble Forskolin Analogues

&
Pages 3783-3795 | Received 05 May 2006, Published online: 01 Dec 2006
 

Abstract

While removing the TBDMS group from OH protection, a novel epoxidation reaction occurred across acrylate ester attached to a forskolin fragment. Besides spectroscopic data, the epoxide formation was confirmed by ring opening with a secondary amine. This unique epoxidation reaction, to our knowledge, is not known in the literature. This reaction led us to discover a simple deblocking protocol. The epoxide and the desired Michael substrates were used to introduce imidazole into forskolin.

Acknowledgements

We gratefully acknowledge R. H. Rupp for his interest and encouragement. We also acknowledge the late A. N. Dohadwalla and N. K. Dadkar for their help in pharmacological screening, P. K. Inamdar and his group for analytical data, and A. Ranade for providing valuable literature information.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.