Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones.
The enantioselective total synthesis of pironetin has been achieved in 11 steps from known aldehyde 2. The synthesis relies on the formation of 5 out of 6 stereocenters through titanium mediated iterative aldol reactions. Key steps in this synthesis include an acetal aldol reaction to establish the stereochemistry at C8 and C9, an acetate aldol reaction, and "Evans" syn aldol reaction.
Crimmins
Michael T
MT
Kenan and Venable Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
Dechert
Anne-Marie R
AM
D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry*; D013871:Thiones / Q000737:chemistry*
D000447:Aldehydes; D011753:Pyrones; D053778:Thiazolidines; D013871:Thiones; C088446:pironetin; C116609:3-hydroxybutanal