Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide The first enantioselective total synthesis of the structurally unique tetraterpenoid, (+)-taiwaniadduct J ( 1 ), has been accomplished via late-stage pericyclic reactions involving an intermolecular Diels–Alder reaction followed by an intramolecular [2 + 2]-cycloaddition reaction. In this reaction, trans -ozic acid methyl ester ( 20 ) serves as the diene (HOMO counterpart) and a p -benzoquinone of abeo -abietane 5 serves as the corresponding LUMO counterpart to affect the [4 + 2]-cycloaddition to set vicinal all-carbon quaternary stereogenic centers. In the process, the first total syntheses of (−)-taiwaniadducts I ( 2 ) and L ( 3 ) were also accomplished. The absolute configuration of (+)-taiwaniadduct J ( 1 ) was confirmed through an enantioselective total synthesis and X-ray analysis. This synthesis demonstrates the elegant application of pericyclic reactions, such as the Diels–Alder cycloaddition and [2 + 2] cycloaddition, to construct multiple quaternary centers in the synthesis of taiwaniadduct J ( 1 ).
Source: JACS Au
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: gold
Estimated APC paid: $3,500
OpenAlex ID: W4407394264