153379-66-9Relevant articles and documents
Highly Enantioselective Approach to Indolizidines: Preparation of (+)-(1S,8aS)-1-Hydroxyindolizidine and (-)-Slaframine
Pourashraf, Mehrnaz,Delair, Philippe,Rasmussen, Martin O.,Greene, Andrew E.
, p. 6966 - 6972 (2007/10/03)
A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether.
Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline
Knight, David W.,Sibley, A. William
, p. 2179 - 2187 (2007/10/03)
The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.
A total synthesis of (-)-slaframine from (+)-cis-(2R,3S)-3-hydroxyproline
Knight,Sibley
, p. 6607 - 6610 (2007/10/02)
A total synthesis of the naturally occurring indolizidine (-)-Slaframine 4 has been achieved, starting from the cis-3-hydroxyproline derivative 1, in which a key step is a Julia olefination reaction using the dianion derived from the β-aminosulfone 5.