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Total synthesis of Dysidiolide:
Reference: Miyaoka, Kajiwara, Hara, Yamada J. Org. Chem. 2001, 66, 1429. DOI
Keywords: Enone -> Allyl-OH • Sulfide -> Sulfone • O-H -> O-C(O)R • Mg-Vinyl+Ketone • Enone-β-OR+Mg-R • Stork-Danheiser • ConjAdd M-SR • O-SiMe2tBu -> O-H • O-H -> O-Bn • Lactone -> Lactol • Aldehyde -> Alkyl-OH • O-H -> O-SiMe2tBu • O-H -> O-P(O)(NR2)2 • Alkyl-OH -> Alkyl-H • Alkyl-OH -> Alkyl-SR • Sulfide -> Sulfone • Li-Sulfone+Alkyl-X • Alkyl-OSO2R -> Alkyl-H • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Wolff-Kishner • Aldehyde -> CH2 • O-THP -> O-H • Alkyl-OH -> Aldehyde • Li-Aryl+Aldehyde • ConjAdd Cu-R • Cu-Me+EnoateEster • Lactone enolate+Alkyl-X • Singlet oxygen+Diene • Furan+Singlet oxygen • Diels-Alder, Yne • Lactone-5 • Mitsunobu -> Ester • Allyl-OH -> Allyl-OAc • Stereoconvergent •
Reagents: AlHiBu2 • Perbenzoic acid, 3-chloro • Carbodiimide • DMAP • Vinyl-MgX • HS-Ph • NEt3 • LiCuMe2 • Fluoride, Bu4N+ • Iodide, Bu4N+ • LiNiPr2 • AlHiBu2 • BH4-Li+ • SiMe2tBu-Cl • P(O)(NMe2)2Cl • TMEDA • Li°/MeNH2 • PBu3 • H2O2 • BuLi(n) • Na(Hg) • Na2HPO4 • Fluoride, Bu4N+ • RuO4-Pr4N+, NMO • Hydrazine • TsOH·Py • RuO4-Pr4N+, NMO • Furyl-Li • Photochemistry • Rose Bengal • O2 (singlet) • PPh3, DEAD •

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