Structural and Synthetic Studies on Maleic Anhydride and Related Diacid Natural Products.

David M Heard, Russell Cox, Thomas J Simpson, Chris L Willis

Research output: Contribution to journalArticle (Academic Journal)peer-review

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Abstract

A concise approach has been developed for the total syntheses of tricladic acids A, B and C previously isolated from Tricladium castaneicola confirming the structures of these fungal natural products. The required (E)-1,3-diene scaffolds were generated with complete stereocontrol via coupling of the appropriate nitronate with an unsaturated bromo-diester which was prepared in 2 steps from citraconic anhydride. The reported structures of the anhydride waquafranone B and the parent diacid were synthesised leading to revision of the originally proposed structure of the natural product and, in accord with Sutherland, confirming that anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated.
Original languageEnglish
JournalTetrahedron
DOIs
Publication statusAccepted/In press - 18 Oct 2019

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Nonadride
  • Natural product synthesis
  • Fungal natural products
  • Structure elucidation

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