Stereoselective synthesis of a monocyclic peloruside a analogue.
The stereoselective synthesis of the monocyclic peloruside A analogue 4 has been achieved, following a new efficient approach for the introduction of the side chain, involving a late-stage addition of vinyl lithium species 7a to aldehyde 8. Further key steps are a highly diastereoselective allyltitanation reaction and a RCM-based macrocyclization.
Wullschleger
Christoph W
CW
Swiss Federal Institute of Technology (ETH) Zürich, HCI H405, Switzerland.
Gertsch
Jürg
J
Altmann
Karl-Heinz
KH
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C414085:peloruside A