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) |
| Reactions: | Ketone → EnolBorane • Aldol-B-Patterson • Ketone → EnolBorane • Ketone enolate+Aldehyde (asym) • O-H → O-SiMe2tBu • Thiazole synthesis • B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • HWE → EnoateEster • HWE → EnoateEster-cis • CarboxAmide → Thioamide • O-H → O-C(O)NR2 • O-H → O-PMB • EnoateEster → Allyl-OH • Allyl-OH → Enal • O-H → O-SiMe2tBu • Ketone → Alkyl-OH • Diol-1,2 cleavage • EnoateEster → Allyl-OH • Alkyl-OH → Aldehyde • HWE → EnoateEster-cis • EnoateEster → Allyl-OH • Allyl-OH → Enal • CarboxAcid → CarboxCl • CarboxCl → CarboxAmide • CarboxEster → Aldehyde • CompRed-CarboxEster/Carbamate+M-H • O-SiMe2tBu → O-H • |
| Reagents: | NEt3 • SiMe2tBu-OTf • BH4-Li+ • Periodate, sodium • KN(SiMe3)2 • 18-crown-6 • AlHiBu2 • Dess-Martin • SOCl2 • SiMe2tBu-Cl • Bromopyruvate • P(O)(OR)2CH2-C(O)OR' • KN(SiMe3)2 • AlHiBu2 • MnO2 • P(O)(OCH2CF3)2CHR-C(O)OMe • Fluoride, R4N+ • O=C(Imid)2 • NH2Me • AlHiBu2 • Crotyl-B(Ipc)2 • Chiral auxiliary (boronate) • KN(SiMe3)2 • 18-crown-6 • P(O)(OCH2CF3)2CHR-C(O)OMe • AlHiBu2 • MnO2 • PMBO-C(=NH)-CCl3 • |