Synthesis 2020; 52(10): 1561-1575
DOI: 10.1055/s-0039-1690794
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues

Mulla Althafh Hussain
,
Faiz Ahmed Khan  ∗
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502285, India   Email: faiz@iith.ac.in
› Author AffiliationsF.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)

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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 condensation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690794.
  • Supporting Information
 

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