Consequences of acid catalysis in concurrent ring opening and halogenation of spiroketals

Consequences of acid catalysis in concurrent ring opening and halogenation of spiroketals

[formula: see text] Lewis and/or Bronsted acid additives permit ring opening and halogenation of spiroketals at substantially reduced temperatures to produce omega-iodo enol ethers in improved yield and purity, which can undergo further reaction in the presence of distal electrophilic centers to giv...

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Veröffentlicht in:Organic letters 1999-12, Vol.1 (11), p.1815-1818
Hauptverfasser: LaCour, T G, Tong, Z, Fuchs, P L
Format: Artikel
Sprache:eng
Schlagworte:
Acids
Catalysis
Halogens
Spiro Compounds - chemical synthesis
Steroids - chemical synthesis
Steroids - chemistry
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Zusammenfassung:[formula: see text] Lewis and/or Bronsted acid additives permit ring opening and halogenation of spiroketals at substantially reduced temperatures to produce omega-iodo enol ethers in improved yield and purity, which can undergo further reaction in the presence of distal electrophilic centers to give new steroid skeletons.
ISSN:1523-7060
DOI:10.1021/ol991078r