Total synthesis of Perillene:
| Reference: | Kondo, K.; Matsumoto, M. Tetrahedron Lett.. 1976, 391. DOI |
| Reactions: | Allyl-X → Allyl-H • Singlet oxygen+Diene • Li-Allyl+Alkyl-X • Allyl-X+Li-R • Allyl-SR → Allyl-H • Allyl-SR → Allyl-H • Furan synthesis • Mechanism • Allylic oxidation → Allyl-OH • Singlet oxygen+Alkene • CompOx-Alkene/Diene+1ΔO2 • Allyl-OH → Allyl-Cl • Li/H → Li-Allyl • |
| Reagents: | O2 (singlet) • S=C(NH2)2 • O2 (singlet) • LiOtBu • SOCl2 • Allyl-Cl • LiCHR-SPh • BuLi(n), HMPA • Li°/NH3 • AlH4-Li+ • Allyl-Li • Allyl-Li • Li°/NH3 • Rose Bengal • S=C(NH2)2 • BuLi(n), HMPA • HMPA (solvent) • LiCHR-SPh • Photochemistry • |