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Total synthesis of Pumiliotoxin B:
Reference: Aoyagi, S.; Hirashima, S.; Saito, K.; Kibayashi, C. J. Org. Chem. 2002, 67, 5517. DOI
Keywords: N-H → N-Boc • N-Boc → N-H • Lactone-5 • EnoateEster → Allyl-OH • Allyl-OH → Allyl-Br • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Ketal → Diol-1,2 • Si-Allenyl+Ketone • Ketone+Si-R • Corey-Fuchs • Cu-SiR3+Propargyl-X • Hydrostannation Alkyne • Li/I → Li-Alkyl • Li-Alkyl → Zn-Alkyl • Takai-Utimoto → Vinyl-I • Sn-Vinyl → I-Vinyl • Pd-Carboxylation • Li-Alkynyl+Aldehyde • N-H → N-Alkyl • Amine-6 • Alkyl-OH → Alkyl-I • Fritsch-Buttenberg-Wiechell • Pd/Zn-Alkyl+Vinyl-X • Negishi coupling •
Reagents: ZnCl2 • BuLi(tert) • PPh3=CBr2 • BuLi(n) • Sulfonyl chloride, methane, NEt3 • CuCN • Allenyl-SiR3 • HfCl2 • Boc2O • HSnPh3 • BEt3 • NIS • Pd(OAc)2 • PPh3 • Acetic acid, trifluoro • AlHiBu2 • PPh3, CBr4 • TASF • SiMe2tBu-OTf • PPh3, I2 • Imidazole • HF·NEt3 • HCl, H2O • CHI3 • Formaldehyde • CO • Pd(PPh3)4

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