departmentof chemistry, chemistry research laboratory, university of oxford… · 2017-06-14 ·...

• SUPPORTING INFORMATION••• Synthesisandbioactivityoffused- andspiro-b-lactone-lactamsystems•• Laia Josa-Culleré,a ChristopherTowers,b FrancesWillenbrock,b ValentineM.Macaulay,b KirstenE.

Christensena andMarkG.Moloney*b•• DepartmentofChemistry,ChemistryResearchLaboratory,TheUniversityofOxford,12Mansfield

Road,Oxford.OX13TA.

• aDepartment ofChemistry,ChemistryResearchLaboratory,UniversityofOxford,12MansfieldRoad,Oxford,OX13TA,UK.E-mail:mark.moloney@chem.ox.ac.uk.

• bDepartment ofOncology,UniversityofOxford,OldRoadCampusResearchBuilding,Oxford,OX37LJ,UK.

• e-mail:mark.moloney@chem.ox.ac.uk•••

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017

NH HO

OCO2Me

O

10

H2O

MeOH

NH HO

OCO2Me

O

10

NO

CO2MeO

OMe

15

NO

CO2MeO

OMe

15

NO

CO2MeO

OBn

16

NO

CO2MeO

OBn

16

NH HO

OCO2Me

OH

17

**

*impurity

H2O

NH HO

OCO2Me

OH

17

NH HO

OCO2Me

OMe

18

H2O

NH HO

OCO2Me

OMe

18

NH HO

OCO2Me

OBn

19

H2O

MeOH

NH HO

OCO2Me

OBn

19

NH HO

OCO2H

OMe

21

H2O

MeOH

*

*impurity

NH HO

OCO2H

OMe

21

NH HO

OCO2H

OBn

22

H2ODCM

*

*impurity

NH HO

OCO2H

OBn

22

NH HO

O

O O

23

H2O

NH HO

O

O O

23

NH O

O

O O

O

24

H2O

NH O

O

O O

O

24

NH O

O

O O

O

24

NH

O

OMe

O

O

26

H2O

NH

O

OMe

O

O

26

N O

MeO2C

O O

28

H2O

N O

MeO2C

O O

28

N O

MeO2C

O OBnO

29

N O

MeO2C

O OBnO

29

NO

CO2MeO

Me OHMe

30a

NO

CO2MeO

Me OHMe

30a

NO

CO2MeO

Me OHMe

30b

NO

CO2MeO

Me OHMe

30b

NO

CO2MeO

Me OHOBn

31a

H2O

NO

CO2MeO

Me OHOBn

31a

NO

OCO2Me

HH

OH

H

MeH

OBn

31a

NO

CO2MeO

Me OHOBn

31b

H2O

NO

CO2MeO

Me OHOBn

31b

NH HO

CO2MeO

Me OHMe

32a

H2O

DCM

NH HO

CO2MeO

Me OHMe

32a

NH HO

CO2MeO

Me OHMe

32b

H2O

NH HO

CO2MeO

Me OHMe

32b

NH HO

CO2MeO

Me OHOBn

33a

H2O

NH HO

CO2MeO

Me OHOBn

33a

NH HO

CO2MeO

Me OHOBn

33b

H2O

NH HO

CO2MeO

Me OHOBn

33b

NH HO

O

Me MeO

O

34 H2O

NH HO

O

Me MeO

O

34

H2O

NH HO

CO2HO

Me OHOBn

47b

NH HO

CO2HO

Me OHOBn

47b

NH HO

O

Me O

O

OBn

35H2O

* *

*impurity

NH HO

O

Me O

O

OBn

35

NH

O O

OMe OHMe

36

H2O

NH

O O

OMe OHMe

36

H2O

DCM*

*impurity

NH HO

CO2HO

Me OHOBn

47a

NH HO

CO2HO

Me OHOBn

47a

NH

O O

OMe OH

37

OBn

H2O

NH

O O

OMe OH

37

OBn

N O

MeO2C

OOBnO

Me

38

N O

MeO2C

OOBnO

Me

38

NO

CO2MeO

Me OHOBn

Me

39

NO

CO2MeO

Me OHOBn

Me

39

NO

OCO2Me

MeH

OH

H

MeH

OBn

39

NH HO

CO2MeO

Me OHOBn

Me

40a

H2O

EtOAcEtOAc

NH HO

CO2MeO

Me OHOBn

Me

40a

NH HO

O

Me O

O

OBn

MeNH

O O

OMe OH

42

OBn

Me43

or

H2O

NH HO

O

Me O

O

OBn

MeNH

O O

OMe OH

42

OBn

Me43

or

NO

CO2MeO

Me OHOH

45

NO

CO2MeO

Me OHOH

45

NO

O

Me HOO

O

46

NO

O

Me HOO

O

46