A highly catalytic asymmetric conjugate addition: synthesis of the C14-C20 fragment of antibiotic TMC-151A, siphonarienal and siphonarienone.
A highly selective and general method for the synthesis of enantiopure deoxypropionates via the iterative application of CuI-Tol-BINAP-catalyzed asymmetric conjugate addition is described. This method gives access to all possible stereoisomers since both syn- and anti-deoxypropionates were obtained in high diastereoselectivities. The usefulness of the method is further exemplified by the preparation of two marine organisms, siphonarienal and siphonarienone, from commercially available trans-2-hexenoate.
Lum
Tze-Keong
TK
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 639798.
Wang
Shun-Yi
SY
Loh
Teck-Peng
TP
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002208:Caproates / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D000900:Anti-Bacterial Agents; D002208:Caproates; D007659:Ketones; D008362:Mannosides; C528456:TMC-151A; C449085:siphonarienal; C528457:siphonarienone; C037652:hexanoic acid