Total synthesis of Butterfly Compound:
| Reference: | Sum, F. W.; Weiler, L. Chem. Commun. 1978, 985. DOI |
| Reactions: | O-THP → O-H • KetoEster dianion+Alkyl-X • Alkyl-X+Enolate • Cu-Me+EnoateEster • ConjAdd-Elimination • ConjAdd Cu-Me • KetoEster dianion+Alkyl-X • Allyl-X+Enolate • Cu-Me+EnoateEster • ConjAdd-Elimination • Allyl-X → Allyl-Br • Finkelstein reaction • EnoateEster → Allyl-OH • Ketone → Enolphosphate • Ketone → EnolPhosphate • O-H → O-SO2Me • |
| Reagents: | Acetoacetate • BuLi(n) • Bromoethanol • P(O)(OR)2Cl • Me-Cuprate • AlH4-Li+ • BuLi(n) • Bromide, lithium • Acetoacetate • BuLi(n) • P(O)(OR)2Cl • Me-Cuprate • NaH • NaH • Sulfonyl chloride, methane • |