Asymmetric Synthesis of the Tetraponerine Alkaloids

• Published in: Journal of organic chemistry Vol. 82; no. 13; pp. 6689 - 6702
• Main Authors: Davies, Stephen G, Fletcher, Ai M, Houlsby, Ian T. T, Roberts, Paul M, Thomson, James E
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.07.2017; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; BETA-AMINO ACIDS; LITHIUM AMIDES; DIASTEREOSELECTIVE CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; AZA-MICHAEL ADDITION; DOUBLE CYCLOISOMERIZATION; RING CLOSING METATHESIS; (+/-)-TETRAPONERINE T6; STEREOSELECTIVE-SYNTHESIS; ALPHA,BETA-UNSATURATED ESTERS

The asymmetric syntheses of all eight tetraponerine alkaloids (T1–T8) were achieved using the diastereoselective conjugate additions of lithium amide reagents in the key stereodefining steps. Conjugate addition of either lithium (R)-N-allyl-N-(α-methylbenzyl)­amide or lithium (R)-N-(but-3-en-1-yl)-N...