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Please login or sign up for a free trial to access the full content. Method 10: Arndt–Eistert and Related Reactions

DOI: 10.1055/sos-SD-020-00757

Phillips, A. J.; Love, C. E.Science of Synthesis, (200720857.

In an analogous vein to the ArndtEistert homologation of acids (see Section, esters can be homologated by conversion into the diazo ketone, Wolff rearrangement, and trapping with an alcohol. For example, acid 61 is readily homologated by conversion into diazo ketone 62 by reaction of the mixed anhydride with (trimethylsilyl)diazomethane and subsequent treatment with methanol in the presence of silver(I) benzoate to yield methyl ester 63 (Scheme 47).[‌145‌] Histidine-derived diazo ketone 64 can be converted into either the methyl ester 65 (R1=Me) or the benzyl ester 65 (R1=Bn) by employing the appropriate alcohol.[‌146‌]

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Meeeeeeeeeee Meeeeeeee

Meeeee (8M)-8-[(eeee-Meeeeeeeeeeeee)eeeee]-8-(8M-eeeeeeee-8-ee)eeeeeeeee (88, M8=Me; Mee-β-MeeMMe); Meeeeee Meeeeeeee:[‌888‌]

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Meeee Meeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

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