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

Bioorg Med Chem. 2019 Jun 15;27(12):2449-2465. doi: 10.1016/j.bmc.2019.02.038. Epub 2019 Feb 19.

Authors

Kevin K W Kuan¹, Adrian W Markwell-Heys¹, Michelle C Cruickshank¹, Denise P Tran¹, Robert M Adlington², Jack E Baldwin², Jonathan H George³

Affiliations

¹ Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia.
² Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK.
³ Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia. Electronic address: jonathan.george@adelaide.edu.au.

PMID: 30992205
DOI: 10.1016/j.bmc.2019.02.038

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Biological Products / chemical synthesis
Biological Products / chemistry*
Biomimetics
Cyclization
Diterpenes / chemistry
Hydroquinones / chemical synthesis*
Hydroquinones / chemistry
Oxidation-Reduction
Porifera / chemistry*
Porifera / metabolism
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Terpenes / chemical synthesis*
Terpenes / chemistry

Substances

Biological Products
Diterpenes
Hydroquinones
Sesquiterpenes
Terpenes
corallidictyal D
liphagal
siphonodictyal B1
corallidictyal A
sclareolide