Total synthesis of Dysidiolide (Yamada):
| Reference: | Miyaoka, H.; Kajiwara, Y.; Hara, Y.; Yamada, Y. J. Org. Chem. 2001, 66, 1429. DOI |
| Reactions: | Sulfide → Sulfoxide • O-H → O-C(O)R • O-SiMe2tBu → O-H • ConjAdd Cu-Me • Cu-Me+EnoateEster • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • Singlet oxygen+Diene • Furan+Singlet oxygen • Diels-Alder, Intram, Yne • Lactone-5 • Bicyclo(440) • Mitsunobu → OC(O)R • Alkyl-OH → Alkyl-OC(O)R • Alkyl-OH inversion • Stereoconvergent • Stork-Danheiser • Enone-β-OR → Enone • Enone+Mg-R • Mg-Vinyl+Ketone • ConjAdd M-SR • Enone+Thiolate • O-H → O-Bn • O-H → O-P(O)X2 • Alkyl-OH → Alkyl-H • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Li/H → Li-Sulfone • Alkyl-X → Alkyl-H • Wolff-Kishner • Aldehyde → CH3 • Li-Aryl+Aldehyde • Alkyl-X → Alkyl-SR • Sulfide → Sulfone • Enone → Allyl-OH • O-SiMe2tBu → O-H • Lactone → Lactol • Aldehyde → Alkyl-OH • O-THP → O-H • Alkyl-OH → Aldehyde • Alkyl-OH → Aldehyde • Sulfoxide-Ei → Ene • Stereoconvergent • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • |
| Reagents: | AlHiBu2 • Perbenzoic acid, 3-chloro • Propiolate • Carbodiimide • Propiolate • DMAP • Vinyl-MgX • Thiol, phenyl • NEt3 • Me-Cuprate • Fluoride, R4N+ • Benzyl-X • LiNiPr2 • AlHiBu2 • BH4-Li+ • SiMe2tBu-Cl • P(O)(NMe2)2Cl • TMEDA • Li°/MeNH2 • PBu3 • H2O2 • BuLi(n) • Na(Hg) • Na2HPO4 • Fluoride, R4N+ • RuO4-Pr4N+, NMO • Hydrazine • TsOH·Py • RuO4-Pr4N+, NMO • Imidazole • Furyl-Li • Photochemistry • Rose Bengal • O2 (singlet) • PPh3, DEAD • NaH • Iodide, R4N+ • Propiolate • |