Stereocontrolled Synthesis of the Portimine Skeleton via Organocatalyst-Mediated Asymmetric Stannylation and Stereoretentive C(<i>sp</i><sup>3</sup>)–C(<i>sp</i><sup>2</sup>) Stille Coupling
Our efforts toward the synthesis of the marine natural product portimine are described. The key to the synthesis of the skeleton is a stereoretentive copper-catalyzed C(<i>sp</i><sup>3</sup>)-C(<i>sp</i><sup>2</sup>) Stille-type cross-coupling that enables the convergent assembly of functionalized fragments. The core skeleton of portimine was constructed via ring-closing metathesis and transannular acetal formation.
Authors
- Atsushi Umehara (ORCID: https://orcid.org/0000-0002-3705-5078)
- Daisuke Sato (ORCID: https://orcid.org/0000-0003-3227-3129)
- Makoto Sasaki (ORCID: https://orcid.org/0000-0003-2964-7986)
Institutions
- Tohoku University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-22
- DOI
- https://doi.org/10.1021/acs.orglett.4c04245
- Citations
- 4
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Japan Society for the Promotion of Science