Assignment of the C5' relative stereochemistry in (+)-lepadin F and (+)-lepadin G and absolute configuration of (+)-lepadin G.
Concise assignments of the C5' stereochemistry in (+)-lepadin F and (+)-lepadin G and the absolute configuration of (+)-lepadin G via the first total syntheses of (+)-5'-epi-lepadin F, (+)-lepadin G, and (+)-5'-epi-lepadin G are described. This work represents an illustrative example in which a diastereomeric pair can possess sufficient spectroscopic difference for clear assignment despite differing only at a highly insulated acyclic stereocenter.
Li
Gang
G
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Hsung
Richard P
RP
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008562:Membrane Glycoproteins; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D008562:Membrane Glycoproteins; D011804:Quinolines; C455162:lepadin F; C455163:lepadin G; C048022:substrate adhesion molecules; D002244:Carbon