Total synthesis of Merrilactone:
| Reference: | Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080-2081. DOI |
| Reactions: | CarboxEster → Alkyl-OH • Lactone-5 • CompE+-CarboxEster/Lactone+H2O • Claisen-Johnson • Diels-Alder, Maleic anhydride • CompE+-Lactone/Lactone+Base • Radical alkylation (Keck) Sn-Allyl • Iodolactonization • Lactone-5 • Aldol-enamine → Enal • Cyclopentene • Epoxidation, peracid • Ozonolysis • Selenide → Selenoxide • Radical cyclization(Vinyl) • Cyclopentane • Bicyclo(330) • Selenoxide-Ei → EneLactone • Lactone → EneLactone • Selenoxide-Ei → Ene-Br • Enal → Allyl-OH • CarboxAcid → CarboxAnhydride • CarboxAnhydride → Alkyl-OH • Lactone-5 • CarboxEster → CarboxEster-α-SeR • Alkene isomerization • O-SiMe2tBu → O-H • Epoxide+M-OR • Ether-4 • CarboxAnhydride → CarboxAcid • CarboxEster → Alkyl-OH • |
| Reagents: | Butadiene, 1-OR • Maleic anhydride • NaOMe • HOMe (react) • O=C(OMe)Cl • BH4-Na+ • Hydroxide, lithium • BH(Et)3-Li+ • O3; PPh3 • Acetic acid, trifluoro • BH4-Na+ • Orthoacetate • Hydroxide, lithium • I2, NaHCO3 • AIBN • LiN(SiMe3)2 • TsOH • TsOH • Allyl-SnR3 • O3 • NEt3 • HSnBu3 • AIBN • SePh-Cl • SePh-Br • Perbenzoic acid, 3-chloro • |