Designer discodermolide segments via ozonolysis of vinyl phosphonates.
To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explored. Successful preparation of the desired aldehyde-esters and lactones from vinyl phosphonates via an oxidative cleavage-phosphite/methanol exchange sequence is described.
Mollat du Jourdin
Xavier
X
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Noshi
Mohammad
M
Fuchs
P L
PL
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000473:Alkanes; D002219:Carbamates; D007783:Lactones; D063065:Organophosphonates; D011753:Pyrones; D013450:Sulfones; D014753:Vinyl Compounds; C009873:divinyl sulfone; D010126:Ozone; C071229:discodermolide