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Total synthesis of Streptazolin:
Reference: Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem. Int. Ed. 2004, 43, 4327. DOI
Keywords: Li-R → Zn-R • O-PMB → O-H • O-SiMe2tBu → O-H • Pd-Diyne reductive cyclization • Al-Alkynyl+Imine • Zn-Alkynyl+Aldehyde • Aldehyde+Zn-R • Felkin-Anh Chelation • N-H → N-Allyl • Amine-6 • O-H → O-C(O)NR2 • Diol-1,2 cleavage • Aldehyde → Imine • N-Allyl → N-H • Pd-Deallylation • N-H → N-C(O)OR • Ketal → Diol-1,2 • Alkyl-OH → Aldehyde-α-OR • O-H → O-SiMe2tBu • O-H → O-SO2R • Felkin-Anh •
Reagents: Periodate, sodium • Allyl-NH2 • Pd2(dba)3 • O=C(OR)Cl • TsOH • Carbonate, potassium • DMSO, (COCl)2 (Swern) • Alkynyl-ZnX • SiMe2tBu-Cl • DDQ • TsCl, Py • SiEt3-Cl • NaH • Fluoride, R4N+ • Pd, formic acid •

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