Premium
A Stereospecific Synthesis of Biotin from an Aromatic Precursor. Preliminary Communication
Author(s) -
Confalone Pat N.,
Pizzolato Giacomo,
Uskoković Milan R.
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590405
Subject(s) - chemistry , biotin , stereospecificity , curtius rearrangement , moiety , yield (engineering) , lactam , total synthesis , stereochemistry , combinatorial chemistry , thiophene , organic chemistry , catalysis , biochemistry , materials science , metallurgy
The total synthesis of the important natural product biotin 1 from the readily available keto diester 3 is described. This approach features the stereospecific hydrogenation of the thiophene intermediate 19 as the key synthetic step. The required differentiation of the diacid functionality of compound 7 is achieved by selective lactam formation with the terminal acid to yield the 8‐membered lactam 8 . A modified Curtius reaction then affords the rearranged diurethane 18 through a series of acyl transfers. Finally, a novel conversion of the 3, 4‐diurethane moiety to the imidazolidone portion of biotin is utilized to complete the synthesis.