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Total synthesis of Archazolid A (Part 1) New:
Reference: Menche, D.; Hassfels, J.; Li, J.; Mayer, K.; Rudolph, S. J. Org. Chem. 2009, 74, 7220. DOI
Keywords: O-H -> O-PMB • O-H -> O-SiMe2tBu • Ketone -> Alkyl-OH • Diol-1,2 cleavage • B-Aldol-Patterson • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • CarboxAcid -> CarboxCl • CarboxCl -> CarboxAmide • O-H -> O-SiMe2tBu • EnoateEster -> Allyl-OH • Allyl-OH -> Enal • O-SiMe2tBu -> O-H • Thiazole • CarboxEster -> Aldehyde • B-Allyl-Ipc+Aldehyde • Brown Crotylation • HWE -> EnoateEster • HWE -> EnoateEster-cis • CarboxAmide -> Thioamide • O-H -> O-C(O)NR2
Reagents: NEt3 • SiMe2tBu-OTf • BH4-Li+ • Periodate, sodium • KN(SiMe3)2 • 18-cr-6 • AlHiBu2 • Dess-Martin • SOCl2 • NH3 • Bromopyruvate • P(O)(OMe)2CH2-CO2R • KN(SiMe3)2 • AlHiBu2 • MnO2 • Fluoride, Bu4N+ • O=C(Im)2 • NH2Me • AlHiBu2 • Crotyl-B(Ipc)2

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