Tetrahedron Letters p. 2653 - 2656 (1997)
Update date:2022-08-16
Topics:
Erbeck, Silke
Prinzbach, Horst
An improved synthetic access to a suitably 'protected' purpurosamine C type glycosyl donor (11, analogously ent-11) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an 'indirect aziridination protocol' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly α-selective glycosylation with an acceptor of known absolute configuration.
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