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Total synthesis of Merrilactone:
Reference: Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080-2081. DOI
Keywords: CarboxAnhydride → Alkyl-OH • Lactone-5 • CarboxEster → Alkyl-OH • Lactone-5 • Enal → Allyl-OH • Claisen-Johnson • Diels-Alder, Maleic anhydride • CompE+-Lactone/Lactone+LiNR2 • CarboxEster → CarboxEster-α-SeR • O-SiMe2tBu → O-H • Alkene isomerization • Epoxide → Diol • Radical alkylation (Keck) Sn-Allyl • Iodolactonization • Lactone-5 • Aldol-enamine → Enone • Epoxidation, peracid • Ozonolysis • Radical cyclization(Vinyl) • Selenoxide-Ei → EneLactone • Lactone → EneLactone • Selenoxide-Ei → Ene-Br •
Reagents: Maleic anhydride • NaOMe • O=C(OR)Cl • BH4-Na+ • Hydroxide, lithium • BH(Et)3-Li+ • O3 • Acetic acid, trifluoro • BH4-Na+ • Orthoacetate • Hydroxide, lithium • I2, NaHCO3 • AIBN • LiN(SiMe3)2 • SePh-Cl • SePh-Br • TsOH • Perbenzoic acid, 3-chloro • TsOH • Allyl-SnR3 • O3 • NEt3 • HSnBu3 • AIBN •

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