Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 46, 2016
Previous Article Next Article

Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

Author affiliations

Abstract

Total syntheses of teadenols A and B, isolated from fermented tea, were accomplished in a highly stereocontrolled manner. Key steps were an organocatalytic asymmetric α-aminoxylation reaction of an aldehyde and a palladium-catalyzed intramolecular allylic substitution with phenol. In the latter reaction, we utilized the different conformational preferences of cyclic and acyclic carbonate precursors to obtain cis- and trans-fused benzopyran rings, respectively, via intramolecular etherification.

Graphical abstract: Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

Back to tab navigation

Supplementary files

Article information


Submitted
12 Sep 2016
Accepted
19 Oct 2016
First published
19 Oct 2016

Org. Biomol. Chem., 2016,14, 10783-10786
Article type
Communication

Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

R. Yoshida, H. Ouchi, A. Yoshida, T. Asakawa, M. Inai, M. Egi, Y. Hamashima and T. Kan, Org. Biomol. Chem., 2016, 14, 10783
DOI: 10.1039/C6OB02004F

Social activity

Search articles by author

Spotlight

Advertisements