Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a Double Sacrificial Chirality Transfer Approach

Philip C Bulman Page; Ross L Goodyear; Alexandra E Horton; Yohan Chan; Rehana Karim; Maria A O'Connell; Christopher Hamilton; Alexandra M Z Slawin; Benjamin R Buckley; Steven M Allin

doi:10.1021/acs.joc.7b02078

Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a Double Sacrificial Chirality Transfer Approach

J Org Chem. 2017 Dec 1;82(23):12209-12223. doi: 10.1021/acs.joc.7b02078. Epub 2017 Nov 20.

Authors

Philip C Bulman Page, Ross L Goodyear, Alexandra E Horton, Yohan Chan, Rehana Karim, Maria A O'Connell, Christopher Hamilton, Alexandra M Z Slawin¹, Benjamin R Buckley², Steven M Allin³

Affiliations

¹ School of Chemistry, University of St Andrews , St Andrews KY16 9ST, Scotland.
² Department of Chemistry, Loughborough University , Loughborough, Leicestershire LE11 3TU, United Kingdom.
³ School of Science & Technology, Nottingham Trent University , Clifton, Nottingham NG11 8NS, United Kingdom.

PMID: 29111711
DOI: 10.1021/acs.joc.7b02078

Abstract

Formal stereocontrolled syntheses of (±)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Leucine / chemistry*
Molecular Structure
Stereoisomerism

Substances

Leucine