1.
Org Lett
; 17(20): 4964-7, 2015 Oct 16.
Article
in English
| MEDLINE
| ID: mdl-26376282
ABSTRACT
A novel synthetic route to the common core structural motif of the stemofoline alkaloids has been developed. The key transformations include (1) an intramolecular 1,3-dipolar cycloaddition reaction of a highly functionalized nitrone, (2) the subsequent formation of a caged structure via lithiated allylic sulfoxide, and (3) the concomitant sila-Pummerer reaction of α-silylalkenyl sulfoxide to prepare a thioester precursor. A series of stereochemistries on the highly caged core structure characteristic of the stemofoline alkaloids was successfully assembled.
Subject(s)
Alkaloids/chemical synthesis , Heterocyclic Compounds, 4 or More Rings/chemical synthesis , Stemonaceae/chemistry , Alkaloids/chemistry , Cycloaddition Reaction , Heterocyclic Compounds, 4 or More Rings/chemistry , Molecular Structure , Nitrogen Oxides/chemistry , Stereoisomerism
2.
Angew Chem Int Ed Engl
; 49(48): 9262-5, 2010 Nov 22.
Article
in English
| MEDLINE
| ID: mdl-21031390