Synthesis of Diastereomeric 8‐Fluoro‐ABC‐Steroid Building Blocks

نویسندگان

چکیده

An eight-step linear sequence for the preparation of two diastereomers an 8-fluoro-ABC-steroid building block was developed. Key step intramolecular Diels–Alder reaction intermediate o-quinodimethane formed from a benzocyclobutene substituted with 5-fluorohex-5-en-4-one chain. This side chain prepared 6-chlorohex-1-ene by bromofluorination, elimination HBr, Finkelstein and alkylation literature-known derivative thus-formed 6-iodo-2-fluorohex-1-ene. Allylic oxidation chain's fluorovinyl moiety to α-fluoro-α,β-unsaturated ketone completed precursor [4+2]-cycloaddition.

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ژورنال

عنوان ژورنال: European Journal of Organic Chemistry

سال: 2023

ISSN: ['1434-193X', '1099-0690']

DOI: https://doi.org/10.1002/ejoc.202300206