Total synthesis of (+/-)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton.
[reaction: see text] The first total synthesis of (+/-)-mycoepoxydiene has been accomplished. A ring-closing olefin metathesis (RCM) approach was employed for the construction of the oxygen-bridged eight-membered bicyclic skeleton. The RCM product was converted to the target natural product featuring the oxidative rearrangement of a furfuryl alcohol introduced as the side chain and the stereoselective 1,2-reduction of a delta-keto-beta,gamma-unsaturated alpha-lactol intermediate.
Takao
Ken-ichi
K
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Watanabe
Gohshi
G
Yasui
Hiroyuki
H
Tadano
Kin-ichi
K
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D034242:Cyclooctanes / Q000138:chemical synthesis; D005658:Fungi / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D008299:Maleic Anhydrides / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*
D001952:Bridged-Ring Compounds; D034242:Cyclooctanes; D005663:Furans; D007783:Lactones; D008299:Maleic Anhydrides; D011753:Pyrones; C476085:mycoepoxydiene; C039281:furan