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

被引：1

作者：

Essers, Michael ^{[1
,2
]}

Haufe, Guenter ^{[1
]}

机构：

[1] Westfal Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany

[2] LANXESS Deutschland GmbH, Chempk Leverkusen, D-51369 Leverkusen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 17期

关键词：

allylic oxidation; annulation; 4+2]-cycloaddition; halofluorination; steroids; DIELS-ALDER REACTIONS; BIOMIMETIC POLYENE CYCLIZATIONS; ANGULAR TRIFLUOROMETHYL GROUP; CATION-STABILIZING AUXILIARY; CHEMICAL CONSEQUENCES; FLUORINE SUBSTITUTION; ALPHA; ALCOHOLS; STEROIDS; QUINODIMETHANES;

D O I：

10.1002/ejoc.202300206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页数：8

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