Total Synthesis of Morusalisin A

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Abstract
Morusalisin A is a nonclassical mulberry Diels-Alder-type adduct (MDAA) with a unique tricyclic skeleton. Herein, we report the first total synthesis of morusalisin A, accomplished in nine steps with an overall yield of 7.3% from commercially available 2,4,6-trihydroxybenzaldehyde. A key feature of the synthesis is a stereoselective intramolecular Diels-Alder (IMDA) reaction of the benzo-tethered butadienyl cinnamate, which efficiently constructs the tricyclic tetrahydro-6H-benzo[c]chromen-6-one core bearing three contiguous stereogenic centers. The pivotal point of the transformation was the strategic placement of a protecting group ortho on the diene moiety, which not only accommodated the IMDA but also controlled the stereochemical outcome. This study is expected to pave the way for broader application of the IMDA strategies in the synthesis of MDAAs, which have predominantly been accessed through intermolecular DA reactions.
Funding Information
  • Chulabhorn Research Institute (53503/4821868)
  • Thailand Science Research and Innovation
  • National Research Council of Thailand (N42A680116)
  • Center of Excellence on Environmental Health and Toxicology, Office of Permanent Secretary, Ministry of Higher Education, Science, Research and Innovation

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