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Synthesis 2020; 52(10): 1561-1575
DOI: 10.1055/s-0039-1690794
DOI: 10.1055/s-0039-1690794
paper
Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues
F.A.K. gratefully acknowledges Science and Engineering Research Board, Department of Science and Technology, New Delhi for financial support.Further Information
Publication History
Received: 18 December 2019
Accepted after revision: 19 December 2019
Publication Date:
27 January 2020 (online)
Abstract
A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.
Key words
total synthesis - Claisen rearrangement - SN2′ reaction - cassumunins A–C - curcumin - Heck reaction - aldol condensationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690794.
- Supporting Information
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