Biotin (Confalone) Confalone, P. N.; Lollar, E. D.; Pizzolato, G.; Uskokovic, M. R. J. Am. Chem. Soc., 1978, 100, 6291.

[answerhappygod]

Biotin Confalone Confalone P N Lollar E D Pizzolato G Uskokovic M R J Am Chem Soc 1978 100 6291 1 (223.65 KiB) Viewed 97 times

Biotin (Confalone) Confalone, P. N.; Lollar, E. D.; Pizzolato, G.; Uskokovic, M. R. J. Am. Chem. Soc., 1978, 100, 6291. 78-06 COMM N-O 1. NBS (60%) 1. NaOET, HOE PhNCO 2. MeC(OJSH, NEt; (71%) 2. ACOCH.CH.NO NET 80% [Allylic oxidation -> Allyl-Br] [Alkyl-X -> Alkyl-SR] [Thiolate+EneNitro] [Cycloaddition Nitrile oxide) =zC0=(0.30 CO th='5 - [Oxime -> Amine] LIAH 92% H MeOC-N H 0 Meo NOH Meo HO H2N Polyphosphoric acid H 1. CI-CO.Me [Beckman rearrangement] [Ketone -> Oxime] 2. DMSO, Ac, 94% [N-H -> N-C(O)OR] [Alkyl-OH -> Ketone] [CarboxAmide -> CarboxAcid] [N-H -> N-C(O)NR.1 1. Ba(OH)2 2. CIC=0 OE н. N "N-H -COH Biotin