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Total synthesis of Archazolid A (Part 1) :
Reference: Menche, D.; Hassfels, J.; Li, J.; Mayer, K.; Rudolph, S. J. Org. Chem. 2009, 74, 7220. DOI (Part 2)
Keywords: O-H → O-PMB • O-H → O-SiMe2tBu • Ketone → Alkyl-OH • Diol-1,2 cleavage • Aldol-B-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 synthesis • CarboxEster → Aldehyde • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • HWE → EnoateEster • HWE → EnoateEster-cis • CarboxAmide → Thioamide • O-H → O-C(O)NR2 • EnoateEster → Allyl-OH •
Reagents: NEt3 • SiMe2tBu-OTf • BH4-Li+ • Periodate, sodium • KN(SiMe3)2 • 18-cr-6 • AlHiBu2 • Dess-Martin • SOCl2 • Bromopyruvate • P(O)(OR)2CH2-CO2R • KN(SiMe3)2 • AlHiBu2 • MnO2 • P(O)(OCH2CF3)2CHR-CO2Me • Fluoride, R4N+ • O=C(Imid)2 • NH2Me • AlHiBu2 • Crotyl-B(Ipc)2 • Chiral auxiliary-Boronate • KN(SiMe3)2 • 18-cr-6 • P(O)(OCH2CF3)2CHR-CO2Me • AlHiBu2 • MnO2

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