Toward the total synthesis of the brasilinolides: construction of a differentially protected C20-C38 segment.
An efficient, convergent synthesis of a differentially protected C20-C38 segment of the brasilinolides is described. Iterative 1,4-syn aldol additions and ketone reductions were employed to construct the two related stereotetrads, while a sequence of Horner-Wadsworth-Emmons (HWE) coupling, CBS reduction, and Sharpless AE installed the epoxy alcohol functionality.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge, UK.
Burton
Paul M
PM
Cordier
Christopher J
CJ
Housden
Michael P
MP
Mühlthau
Friedrich A
FA
Loiseleur
Olivier
O
D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans; D013237:Stereoisomerism
D007659:Ketones; D018942:Macrolides; D011714:Pyrans; C111141:brasilinolide A; C406050:brasilinolide B; C484617:brasilinolide C