%0 Journal Article %A Takao, Ken-ichi %A Yasui, Hiroyuki %A Yamamoto, Shun %A Sasaki, Daisuke %A Kawasaki, Soujiro %A Watanabe, Gohshi %A Tadano, Kin-ichi %D 2004 %T Asymmetric Total Syntheses of (+)-Mycoepoxydiene and Related Natural Product (−)-1893A:  Application of One-Pot Ring-Opening/Cross/Ring-Closing Metathesis to Construct Their 9-Oxabicyclo[4.2.1]nona-2,4-diene Skeleton %U https://acs.figshare.com/articles/journal_contribution/Asymmetric_Total_Syntheses_of_Mycoepoxydiene_and_Related_Natural_Product_1893A_Application_of_One_Pot_Ring_Opening_Cross_Ring_Closing_Metathesis_to_Construct_Their_9_Oxabicyclo_4_2_1_nona_2_4_diene_Skeleton/3312673 %R 10.1021/jo048566j.s002 %2 https://acs.figshare.com/ndownloader/files/5151403 %K oxidative rearrangement %K mycoepoxydiene %K sequential metathesis product %K oxabicyclo %K furfuryl alcohol %K strategy features %K vinylogous aldol reaction %K ROM %K RCM %X The total syntheses of (+)-mycoepoxydiene and (−)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2-ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (−)-1893A was also synthesized via the vinylogous aldol reaction. %I ACS Publications