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

Satya Kumar Avula 
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 AffiliationsThe authors would like to thank the University of Nizwa for the generous support of this project.
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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.

Keywords

Surinamensinol A B - anti-inflammatory and antitumour neolignans - stereoselective total synthesis - Suzuki–Miyaura cross coupling - Mitsunobu reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707325.
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Publication History

Received: 08 September 2020

Accepted after revision: 24 September 2020

Article published online:
15 October 2020

© 2020. The Author(s). 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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