Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of beta-hydroxycarbonyl compounds.
A versatile approach for the enantioselective synthesis of functionalised beta-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of acyloxazolidinone using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted delta-lactones.
Le Sann
Christine
C
School of Chemistry, University of Bristol, Cantock's Close, Bristol, UKBS8 1TS.
Munoz
Dulce M
DM
Saunders
Natalie
N
Simpson
Thomas J
TJ
Smith
David I
DI
Soulas
Florilène
F
Watts
Paul
P
Willis
Christine L
CL
D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D007659:Ketones; D018942:Macrolides