New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of Solamin.
An original convergent total synthesis of Solamin (type A annonaceous acetogenin) was achieved. The central THF core was obtained by means of a ring-closing metathesis (RCM) reaction using a ruthenium imidazolylidene complex. The RCM substrate was prepared from a vinyl-substituted epoxide by reaction with an allyl alcohol, both synthesized from propargylic alcohol. The flexibility of the strategy should be useful in preparing various natural and unnatural annonaceous acetogenins.
CEA, CE-Saclay, Service de Marquage Moléculaire et de Chimie Bioorganique, Bât 547, Département de Biologie Joliot-Curie, 91191 Gif Sur Yvette, France.
Guillaume
G
Prestat
Christophe
C
Baylon
Marie-Pierre
MP
Heck
Gabriela A
GA
Grasa
Steven P
SP
Nolan
Charles
C
Mioskowski
D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry*; D001558:Benzethonium / Q000138:chemical synthesis*; D002384:Catalysis; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; D001558:Benzethonium; D012428:Ruthenium