A synthesis of the pyrrolizidine alkaloids (-)-heliotridane and (-)-isoretronecanol and their epimers is described. The key step involves a daistereoselective conjugate addition of organocuprates to (2S)-N-(tert-butoxycarbonyl)-2-[(E)-3'-methoxy-3'-oxo-1'-propenyl]pyrrolidine (2) deriving from (S)-proline.
Lecoz, S., Mann, A., Thareau, F., Taddei, M. (1993). Synthesis of (-)-heliotridane and (-)-isoretronecanol Via Diastereoselective Conjugate Addition of Organocuprates To An Enoate Deriving From Proline. HETEROCYCLES, 36(9), 2073-2079 [10.3987/com-93-6423].
Synthesis of (-)-heliotridane and (-)-isoretronecanol Via Diastereoselective Conjugate Addition of Organocuprates To An Enoate Deriving From Proline
Taddei, Maurizio
1993-01-01
Abstract
A synthesis of the pyrrolizidine alkaloids (-)-heliotridane and (-)-isoretronecanol and their epimers is described. The key step involves a daistereoselective conjugate addition of organocuprates to (2S)-N-(tert-butoxycarbonyl)-2-[(E)-3'-methoxy-3'-oxo-1'-propenyl]pyrrolidine (2) deriving from (S)-proline.
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https://hdl.handle.net/11365/31041
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