Forwards and backwards - synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C-F

Laurefurenynes C-F are four natural products isolated from Laurencia species whose structures were originally determined on the basis of extensive nuclear magnetic resonance experiments. On the basis of a proposed biogenesis, involving a tricyclic oxonium ion as a key intermediate, we have reassigne...

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Published inChemical science (Cambridge) Vol. 11; no. 42; pp. 11592 - 11600
Main Authors Chan, Hau Sun Sam, Thompson, Amber L., Christensen, Kirsten E., Burton, Jonathan W.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.11.2020
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Biomimetics
Chemistry
Chemistry, Multidisciplinary
Crystallography
Enantiomers
Natural products
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
Synthesis
MARINE RED ALGA
ABSOLUTE-CONFIGURATION
FORMAL SYNTHESIS
STEREOCHEMISTRY
ORIGIN CHEMISTRY
CRYSTAL-STRUCTURES
CIS-2-ETHYL-8-FORMYL-3,4,7,8-DIHYDRO-2H-OXOCIN-3-ONE 3-ETHYLENE ACETAL
STEREOSELECTIVE-SYNTHESIS
REDUCTION-ELIMINATION
STRUCTURE CONFIRMATION
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Summary:Laurefurenynes C-F are four natural products isolated from Laurencia species whose structures were originally determined on the basis of extensive nuclear magnetic resonance experiments. On the basis of a proposed biogenesis, involving a tricyclic oxonium ion as a key intermediate, we have reassigned the structures of these four natural products and synthesized the four reassigned structures using a biomimetic approach demonstrating that they are the actual structures of the natural products. In addition, we have developed a synthesis of the enantiomers of the natural products laurencin and deacetyllaurencin from the enantiomer of (E)-laurefucin using an unusual retrobiomimetic strategy. All of these syntheses have been enabled by the use of tricyclic oxonium ions as pivotal synthetic intermediates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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Authors to whom correspondence regarding X-ray crystallography should be addressed.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc04120c