Premium
Synthesis of 5,6‐carbonyldioxyindole, a melanogenic cyclic carbonate ester of 5,6‐dihydroxyindole
Author(s) -
Lutz Wilson B.,
Mcnamara Craig R.,
Olinger Max R.,
Schmidt David F.,
Doster Douglas E.,
Fiedler Mark D.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210451
Subject(s) - chemistry , hydrolysis , derivative (finance) , melanin , tyrosine , stereochemistry , organic chemistry , biochemistry , financial economics , economics
Abstract 5,6‐Carbonyldioxyindole ( 4 ), a melanogenic derivative of 5,6‐dihydroxyindole ( 1 ), was synthesized by a procedure starting with 3,4‐methylenedioxycinnamic acid ( 5 ). Compound 4 is a stable crystalline solid which is readily hydrolyzed to 1 , a key intermediate on the biosynthetic pathway from tyrosine to melanin.