Radical-Induced Ring Opening of Epoxysilane in the Synthesis of (±)-Supinidine and (±)-Trachelanthamidine

Autor:	Yeun-Min Tsai, Bor‐Wen Ke
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Silylation Stereochemistry Radical Triethylborane Tributyltin hydride Ether General Chemistry Silyl enol ether Hydrogen atom abstraction Aldehyde Medicinal chemistry chemistry.chemical_compound chemistry
Zdroj:	Journal of the Chinese Chemical Society. 40:641-642
ISSN:	0009-4536
DOI:	10.1002/jccs.199300102
Popis:	An α-(2-silyloxiranyl)carbinyl radical fused to a pyrrolizidine skeleton was generated from the corresponding bromide 4. This radical underwent rearrangements followed by hydrogen abstraction to give silyl allyl ether 8 and silyl enol ether 9. The mixture was converted to (±)-supinidine 1 and (±)-trachelanthamidine 3. When triethylborane/oxygen was used to initiate the radical reaction, an α,β-unsaturated aldehyde 15 was obtained, thus to accomplish a formal synthesis of (±)-1.
Databáze:	OpenAIRE
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