Details
| Original language | English |
|---|---|
| Article number | 130717 |
| Journal | TETRAHEDRON |
| Volume | 76 |
| Issue number | 1 |
| Early online date | 31 Oct 2019 |
| Publication status | Published - 3 Jan 2020 |
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 cyclic anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated.
Keywords
- Fungal natural products, Natural product synthesis, Nonadride, Structure elucidation, Tricladic acid
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: TETRAHEDRON, Vol. 76, No. 1, 130717, 03.01.2020.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Structural and synthetic studies on maleic anhydride and related diacid natural products
AU - Heard, David M.
AU - Tayler, Emyr R.
AU - Cox, Russell J.
AU - Simpson, Thomas J.
AU - Willis, Christine L.
N1 - Funding information: We are grateful to the EPSRC (EP/L015366/1), Bristol Chemical Synthesis Centre for Doctoral Training, which provided a PhD studentship for DMH.
PY - 2020/1/3
Y1 - 2020/1/3
N2 - 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 cyclic anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated.
AB - 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 cyclic anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated.
KW - Fungal natural products
KW - Natural product synthesis
KW - Nonadride
KW - Structure elucidation
KW - Tricladic acid
UR - http://www.scopus.com/inward/record.url?scp=85075885475&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2019.130717
DO - 10.1016/j.tet.2019.130717
M3 - Article
AN - SCOPUS:85075885475
VL - 76
JO - TETRAHEDRON
JF - TETRAHEDRON
SN - 0040-4020
IS - 1
M1 - 130717
ER -