CC BY-NC-ND 4.0 · SynOpen 2020; 04(04): 84-88
DOI: 10.1055/s-0040-1707325
paper

Total Synthesis of Surinamensinols A and B

a  Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman   Email: aharrasi@unizwa.edu.om
,
Biswanath Das
a  Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman   Email: aharrasi@unizwa.edu.om
,
Rene Csuk
b  Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120, Halle (Saale), Germany
,
Ahmed Al-Rawahi
a  Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman   Email: aharrasi@unizwa.edu.om
,
Ahmed Al-Harrasi
a  Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman   Email: aharrasi@unizwa.edu.om
› Author Affiliations
The authors would like to thank the University of Nizwa for the generous support of this project.


Abstract

An efficient total synthesis of the naturally occurring anti-inflammatory and antitumour 8-O-4′-neolignans, surinamensinols A and B, has been accomplished from commercially available allyl alcohol and (S)-ethyl lactate. The synthetic sequence involves a palladium-catalysed Suzuki–Miyaura cross-coupling reaction followed by a chiral Mitsunobu­ reaction as the key steps. This is the first report of the simultaneous stereoselective total synthesis of surinamensinols A and B through a single approach involving only six steps.

Supporting Information



Publication History

Received: 08 September 2020

Accepted after revision: 24 September 2020

Publication Date:
15 October 2020 (online)

© 2020. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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