Toward the total synthesis of the brasilinolides: stereocontrolled assembly of a C1-C19 polyol segment.
Two highly convergent syntheses of a fully protected C1-C19 polyol subunit of the brasilinolide family of immunosuppressive macrolides are described, exploiting boron-mediated 1,5-anti aldol couplings to form the C8-C9 and C13-C14 bonds.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk
Mühlthau
Friedrich A
FA
Cordier
Christopher J
CJ
Housden
Michael P
MP
Burton
Paul M
PM
Loiseleur
Olivier
O
D000447:Aldehydes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D018942:Macrolides; D011108:Polymers; C024617:polyol; D002244:Carbon; C116609:3-hydroxybutanal