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

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

doi:10.1016/j.tet.2019.130717

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

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

School of Chemistry

Research output: Contribution to journal › Article (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 language	English
Journal	Tetrahedron
DOIs	https://doi.org/10.1016/j.tet.2019.130717
Publication status	Accepted/In press - 18 Oct 2019

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Keywords

Nonadride
Natural product synthesis
Fungal natural products
Structure elucidation

Access to Document

10.1016/j.tet.2019.130717

Full-text PDF (author’s accepted manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Elsevier at https://doi.org/10.1016/j.tet.2019.130717 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 729 KBLicence: CC BY-NC-ND

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Understanding Programming in Highly Reducing Iterative Fungal Polyketide Synthases - a Structural and Mechanistic Approach
Simpson, T. J. (Principal Investigator)
1/07/11 → 1/01/15
Project: Research

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title = "Structural and Synthetic Studies on Maleic Anhydride and Related Diacid Natural Products.",

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.",

keywords = "Nonadride, Natural product synthesis, Fungal natural products, Structure elucidation",

author = "Heard, \{David M\} and Russell Cox and Simpson, \{Thomas J\} and Willis, \{Chris L\}",

year = "2019",

month = oct,

day = "18",

doi = "10.1016/j.tet.2019.130717",

language = "English",

journal = "Tetrahedron",

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TY - JOUR

T1 - Structural and Synthetic Studies on Maleic Anhydride and Related Diacid Natural Products.

AU - Heard, David M

AU - Cox, Russell

AU - Simpson, Thomas J

AU - Willis, Chris L

PY - 2019/10/18

Y1 - 2019/10/18

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 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 anhydrides with exo-dienes are unstable. Biomimetic dimerisations of the proposed monomers of the nonadride scytalidin were investigated.

KW - Nonadride

KW - Natural product synthesis

KW - Fungal natural products

KW - Structure elucidation

U2 - 10.1016/j.tet.2019.130717

DO - 10.1016/j.tet.2019.130717

M3 - Article (Academic Journal)

SN - 0040-4020

JO - Tetrahedron

JF - Tetrahedron

ER -

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

Abstract

Research Groups and Themes

Keywords

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Projects

Understanding Programming in Highly Reducing Iterative Fungal Polyketide Synthases - a Structural and Mechanistic Approach

Cite this