10.1021/jo201005d.s001
Lorenzo
V. White
Lorenzo
V.
White
Brett D. Schwartz
Brett D.
Schwartz
Martin G. Banwell
Martin G.
Banwell
Anthony C. Willis
Anthony C.
Willis
A Chemoenzymatic Total Synthesis of (+)-Clividine
American Chemical Society
2011
ci
alkaloid
ee
clividine
enantiomerically
C 11b
ent
enantiomeric
stereochemistry
Synthesi
diastereoselective addition
ClividineThe
material
Chemoenzymatic
pendant cyclohexene
compound
synthesis
2011-08-05 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/A_Chemoenzymatic_Total_Synthesis_of_Clividine/2625578
The title compound, <i>ent</i>-<b>1</b>, the non-natural
enantiomeric form of the lycorenine-type alkaloid (−)-clividine
(<b>1</b>), has been prepared using the enantiomerically pure
(ee >99.8%) <i>cis</i>-1,2-dihydrocatechol <b>3</b> as starting material. A key feature associated with the
closing stages of the synthesis involved the diastereoselective addition
of a nitrogen-centered radical onto a pendant cyclohexene to establish
the cis-fused D-ring and the required stereochemistry at C11b in the
final product <i>ent</i>-<b>1</b>.