Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D

Kevin K.W. Kuan; Adrian W. Markwell-Heys; Michelle C. Cruickshank; Denise P. Tran; Robert M. Adlington; Jack E. Baldwin; Jonathan H. George

doi:10.1016/j.bmc.2019.02.038

Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D

Kevin K.W. Kuan, Adrian W. Markwell-Heys, Michelle C. Cruickshank, Denise P. Tran, Robert M. Adlington, Jack E. Baldwin, Jonathan H. George

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The marine sponge Aka coralliphaga is a rich source of biologically active and structurally interesting meroterpenoids. Inspired by these natural products, we have used biosynthetic speculation to devise biomimetic syntheses of siphonodictyal B, liphagal and corallidictyals A–D from sclareolide. This work resulted in the development of new cascade reactions in the synthesis of liphagal, the reassignment of the structure of siphonodictyal B, and the realisation that corallidictyals A and B are possibly isolation artefacts.

Original language	English
Pages (from-to)	2449-2465
Number of pages	17
Journal	Bioorganic and Medicinal Chemistry
Volume	27
Issue number	12
DOIs	https://doi.org/10.1016/j.bmc.2019.02.038
Publication status	Published or Issued - 15 Jun 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2019.02.038

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Kuan, K. K. W., Markwell-Heys, A. W., Cruickshank, M. C., Tran, D. P., Adlington, R. M., Baldwin, J. E., & George, J. H. (2019). Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D. Bioorganic and Medicinal Chemistry, 27(12), 2449-2465. https://doi.org/10.1016/j.bmc.2019.02.038

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title = "Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D",

abstract = "The marine sponge Aka coralliphaga is a rich source of biologically active and structurally interesting meroterpenoids. Inspired by these natural products, we have used biosynthetic speculation to devise biomimetic syntheses of siphonodictyal B, liphagal and corallidictyals A–D from sclareolide. This work resulted in the development of new cascade reactions in the synthesis of liphagal, the reassignment of the structure of siphonodictyal B, and the realisation that corallidictyals A and B are possibly isolation artefacts.",

author = "Kuan, {Kevin K.W.} and Markwell-Heys, {Adrian W.} and Cruickshank, {Michelle C.} and Tran, {Denise P.} and Adlington, {Robert M.} and Baldwin, {Jack E.} and George, {Jonathan H.}",

note = "Publisher Copyright: {\textcopyright} 2019",

year = "2019",

month = jun,

day = "15",

doi = "10.1016/j.bmc.2019.02.038",

language = "English",

volume = "27",

pages = "2449--2465",

journal = "Bioorganic and Medicinal Chemistry",

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Kuan, KKW, Markwell-Heys, AW, Cruickshank, MC, Tran, DP, Adlington, RM, Baldwin, JE & George, JH 2019, 'Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D', Bioorganic and Medicinal Chemistry, vol. 27, no. 12, pp. 2449-2465. https://doi.org/10.1016/j.bmc.2019.02.038

Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D. / Kuan, Kevin K.W.; Markwell-Heys, Adrian W.; Cruickshank, Michelle C. et al.
In: Bioorganic and Medicinal Chemistry, Vol. 27, No. 12, 15.06.2019, p. 2449-2465.

Research output: Contribution to journal › Article › peer-review

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T1 - Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga

T2 - Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D

AU - Kuan, Kevin K.W.

AU - Markwell-Heys, Adrian W.

AU - Cruickshank, Michelle C.

AU - Tran, Denise P.

AU - Adlington, Robert M.

AU - Baldwin, Jack E.

AU - George, Jonathan H.

PY - 2019/6/15

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Biomimetic synthetic studies on meroterpenoids from the marine sponge Aka coralliphaga: Divergent total syntheses of siphonodictyal B, liphagal and corallidictyals A–D

Abstract

ASJC Scopus subject areas

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