First total synthesis of (+/-)-taxifolial a and (+/-)-iso-caulerpenyne.
The first synthesis of (+/-)-taxifolial A and iso-caulerpenyne was accomplished. The key steps in the sequence are (1) the stereoselective assembly of a vinyltin derived from butynediol and a functionalized aldehyde and (2) the construction of the dienyne moiety via a Stille cross-coupling.
Commeiras
L
L
Laboratoire de Synthèse Organique associé au CNRS (UMR 6009), Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France.
Santelli
M
M
Parrain
J L
JL
D000447:Aldehydes / Q000138:chemical synthesis*; D000475:Alkenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000138:chemical synthesis*; D009947:Organotin Compounds / Q000737:chemistry; D012624:Seaweed / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D007202:Indicators and Reagents; D008387:Marine Toxins; D009947:Organotin Compounds; D012717:Sesquiterpenes; C431063:taxifolial A; C097889:caulerpenyne