✍ Scribed by B.N. Naidu; F.G. West
No coin nor oath required. For personal study only.
Diazoketone 5b, available in one step from proline benzyl ester, underwent conversion to quinolizidine gb with high diastereoseleOivity (19:1 gb/Tb) and in sm~risingly high enanfiomeric excess (75%). The key step presumably occurs via spirocyclic ylide 6b, which undergoes [l,2]-shift with retention. Rean'angement product Sb was converted to (-)-epilupinine 2 via an efficient, 3-step sequence.
📜 SIMILAR VOLUMES
A short and high yielding enantioselective synthesis of (À)-bestatin, a naturally occurring aminopeptidase inhibitor, is described via L-proline-catalyzed asymmetric a-amination of 3-phenylpropionaldehyde as the key reaction. The methodology also involves a Pd-catalyzed intramolecular cyclization of
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract For Abstract see ChemInform Abstract in Full Text.
A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a d-azidolactone was