Formal synthesis of (+)-lactacystin from l-serine

Philip C Bulman Page; Ross L Goodyear; Yohan Chan; Alexandra M Z Slawin; Steven M Allin

doi:10.1039/c9ra07244f

Formal synthesis of (+)-lactacystin from l-serine

RSC Adv. 2019 Sep 24;9(51):30019-30032. doi: 10.1039/c9ra07244f. eCollection 2019 Sep 18.

Authors

Philip C Bulman Page¹, Ross L Goodyear¹, Yohan Chan¹, Alexandra M Z Slawin², Steven M Allin³

Affiliations

¹ School of Chemistry, University of East Anglia, Norwich Research Park Norwich Norfolk NR4 7TJ UK p.page@uea.ac.uk.
² School of Chemistry, University of St Andrews St Andrews Scotland KY16 9ST UK.
³ School of Science & Technology, Nottingham Trent University Clifton Nottingham NG11 8NS UK.

Abstract

A formal, stereocontrolled synthesis of lactacystin has been completed from t-Bu-O-l-serine, providing the key intermediate 13, also useful for the generation of a range of C-9 analogues.