Stereoselective synthesis of the C1-C13 fragment of (+)-discodermolide using asymmetric allyltitanations.
[reaction: see text] The synthesis of the C1-C13 fragment of (+)-discodermolide has been achieved. The configurations of the stereogenic centers have been controlled by enantioselective allyl- and crotyltitanations of aldehydes, and the Z configuration of the olefin at C8-C9 was controlled by a ring-closing metathesis.
BouzBouz
Samir
S
Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin 75231, Paris Cedex 05, France. samir.bouzbouz@espci.fr
Cossy
Janine
J
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes; D000475:Alkenes / Q000737:chemistry; D000818:Animals; D002219:Carbamates; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011753:Pyrones; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D000475:Alkenes; D002219:Carbamates; D007783:Lactones; D011753:Pyrones; C071229:discodermolide