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Synthesis 2022; 54(02): 465-474
DOI: 10.1055/a-1628-7972
DOI: 10.1055/a-1628-7972
paper
Dihydroxylation Studies of Isoquinolinones: Synthesis of the EF-Ring of Lysolipin I
Generous financial support by the DFG (TRR 261) is gratefully acknowledged.
Abstract
Inspired by the potent polycyclic xanthone antibiotic lysolipin I, a general study on asymmetric dihydroxylation reactions of variously substituted isoquinolinones was performed. Different isoquinolinones were efficiently prepared, either by a Pomeranz–Fritsch type condensation or a Curtius rearrangement. Under a broad variety of conventional oxygenation procedures, they proved very unreactive. However, either by suitable substitution of the appending aromatic ring or more forcing conditions a dihydroxylation could finally be performed, which allowed the synthesis of the EF-ring of lysolipin I.
Key words
lysolipin I - Pomeranz–Fritsch cyclization - Curtius rearrangement - asymmetric dihydroxylation - isoquinolinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1628-7972.
- Supporting Information
Publication History
Received: 09 July 2021
Accepted after revision: 01 September 2021
Accepted Manuscript online:
01 September 2021
Article published online:
14 October 2021
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