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The Total Synthesis of (±)‐Mitomycin K
Author(s) -
Benbow John W.,
Schulte Gayle K.,
Danishefsky Samuel J.
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199209151
Subject(s) - azide , chemistry , mitomycin c , total synthesis , imidazole , stereochemistry , bioorganic chemistry , double bond , organic chemistry , biology , genetics , enzyme
The use of (phenylthio)methyl azide to build the N ‐methylaziridine unit and a provocative rearrangement to an imidazoledithiocarboxyl group are the crucial steps in the total synthesis of (±)‐mitomycin K ( 3 ) via 1 and 2 . Mitomycins of type 3 promise to provide an interesting bioorganic chemistry because of the exocyclic double bond. X = H, Y = OH, R = SC(S)‐imidazole.