Intermolecular Oxidopyrylium\n(5 + 2) Cycloaddition/Reductive\nRing-Opening Strategy for the Synthesis of α‑Methoxytropones

α-Methoxytropone is a structural motif found in\nvarious natural\nproducts and other compounds of interest to the scientific community\nbut remains a synthetic challenge. The present Note describes the\nsynthesis of variously substituted α-methoxytropones and related\ncompounds through an intermolecular 3-hydroxy-4-pyrone-based oxidopyrylium\n(5 + 2) cycloaddition followed by a samarium iodide-mediated reductive\nring-opening. The strategy is highlighted in the synthesis of a novel\nAC-ring analogue of colchicine to compare it to existing methods.

Publication Details

Journal
Figshare
Published
2024-11-12
DOI
https://doi.org/10.1021/acs.joc.4c01989.s001
Primary Topic
Wheat and Barley Genetics and Pathology
Type
article
Field-Weighted Citation Impact
0.00
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article

Intermolecular Oxidopyrylium\n(5 + 2) Cycloaddition/Reductive\nRing-Opening Strategy for the Synthesis of α‑Methoxytropones

Figshare
Wheat and Barley Genetics and Pathology
article

Intermolecular Oxidopyrylium\n(5 + 2) Cycloaddition/Reductive\nRing-Opening Strategy for the Synthesis of α‑Methoxytropones

article en

Abstract

α-Methoxytropone is a structural motif found in\nvarious natural\nproducts and other compounds of interest to the scientific community\nbut remains a synthetic challenge. The present Note describes the\nsynthesis of variously substituted α-methoxytropones and related\ncompounds through an intermolecular 3-hydroxy-4-pyrone-based oxidopyrylium\n(5 + 2) cycloaddition followed by a samarium iodide-mediated reductive\nring-opening. The strategy is highlighted in the synthesis of a novel\nAC-ring analogue of colchicine to compare it to existing methods.

Figshare
Openalex Percentile: Top 39%
Wheat and Barley Genetics and Pathology
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Intermolecular Oxidopyrylium\n(5 + 2) Cycloaddition/Reductive\nRing-Opening Strategy for the Synthesis of α‑Methoxytropones · Figshare (2024) | TGRS Research Map | TGRS