departmentof chemistry, chemistry research laboratory, university of oxford… · 2017-06-14 ·...
TRANSCRIPT
• 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:[email protected].
• bDepartment ofOncology,UniversityofOxford,OldRoadCampusResearchBuilding,Oxford,OX37LJ,UK.
• e-mail:[email protected]•••
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