Total synthesis of Lanceol:
| Reference: | Shimada, J.; Hashimoto, K.; Kim, B. H.; Nakamura, E.; Kuwajima, I J. Am. Chem. Soc. 1984, 106, 1759 DOI |
| Reactions: | Acyloin • Cyclobutane • EnoateEster → Allyl-OH • Takai-Lombardo → Ene • Ketone → C=CH2 • Wittig-carboxymethyl → EnoateEster • Alkene isomerization-EZ • Mechanism • Mukaiyama Aldol • Aldol-Si • CarboxEster → Alkyl-OH • CarboxAcid → CarboxEster • Alkyl-OH → Aldehyde • CarboxEster → CarboxAcid • |
| Reagents: | Na/K • SiMe3-Cl • Hydroxide, sodium • CH2Br2 • Diazomethane • AlH4-Li+ • CrO3·Py2 (Collins) • PPh3=C(Me)-CO2R • Photochemistry • AlH3 • SnCl4 • SnCl4 • |