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Radical‐Induced Ring Opening of Epoxysilane in the Synthesis of (±)‐Supinidine and (±)‐Trachelanthamidine
Author(s) -
Tsai YeunMin,
Ke BorWen
Publication year - 1993
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199300102
Subject(s) - chemistry , triethylborane , silyl enol ether , radical cyclization , silylation , silyl ether , aldehyde , hydrogen atom abstraction , pyrrolizidine , ether , ring (chemistry) , enol , medicinal chemistry , radical , organic chemistry , stereochemistry , catalysis
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 .