Work

Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction

Year: 2024

Type: article

Abstract: The synthesis of the spirocyclic imine fragment of the portimine family of marine toxins has been achieved. A densely functionalized key lactone-ester intermediate was assembled via a highly diastereoselective Diels-Alder cycloaddition, involving a novel γ-hydroxymethyl-α,β-butenolide dienophile. A Stille coupling was employed to install the vinyl group. Selective elaboration of the two carbonyl groups successfully afforded the spirocyclic imine fragment.

Source: ACS Omega

DOI: 10.1021/acsomega.4c08699

Authors: Ze Kuang, Xiao-Bo Ding, Freda F. Li, Margaret A. Brimble

Institutions: University of Auckland, Maurice Wilkins Centre

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funder: Maurice Wilkins Centre for Molecular Biodiscovery