Synthesis of the Spermidine Alkaloids (−)??(2R, 3R)??and (−)??(2R, 3S)??3??Hydroxycelacinnine: Macrocyclization with Oxirane??Ring Opening and Inversion via Cyclic …
NA Khanjin, M Hesse
Index: Khanjin, Nikolai A.; Hesse, Manfred Helvetica Chimica Acta, 2003 , vol. 86, # 6 p. 2028 - 2057
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Citation Number: 11
Abstract
Abstract The two epimers (−)-1a and (−)-1b of the macrocyclic lactam alkaloid 3- hydroxycelacinnine with the (2R, 3R) and (2R, 3S) absolute configurations, respectively, were synthesized by an alternative route involving macrocyclization with the regio-and stereoselective oxirane-ring opening by the terminal amino group (Schemes 2 and 6). Properly N-protected chiral trans-oxirane precursors provided (2R, 3R)-macrocycles after ...
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