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Synthesis 2023; 55(09): 1322-1327
DOI: 10.1055/s-0042-1751422
DOI: 10.1055/s-0042-1751422
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Biogenesis-Inspired Synthesis of Penicillitone
Financial support for this work was provided by the European Research Council (ERC Consolidator Grant ‘RadCrossSyn’, agreement no. 101043353), Deutsche Forschungsgemeinschaft (Heisenberg-Program HE 7133/8-1), and Boehringer Ingelheim Stiftung (plus3 perspectives program).
Abstract
The biogenesis-inspired synthesis of the structurally unique 15(14→11)abeo-steroid penicillitone starting from commercially available ergosterol is reported. Key to the strategy is an intramolecular vinylogous aldol reaction of a 14,15-secoergostane obtained from the previously reported 14,15-secosteroid platform. Since a similar intermediate has been employed to access the strophasterol class of natural products, this work points at a possible biosynthetic connection between penicillitone and the strophasterols.
Key words
abeo-steroids - biogenesis-inspired synthesis - intramolecular vinylogous aldol reaction - penicillitone - strophasterolSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751422.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. Januar 2023
Angenommen nach Revision: 19. Januar 2023
Artikel online veröffentlicht:
23. Februar 2023
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