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A Method for the Introduction of Reporter Groups into Moenomycin A, Based on Thiouronium Salt Chemistry
Author(s) -
Buchynskyy Andrij,
Stembera Katherina,
Hennig Lothar,
Findeisen Matthias,
Giesa Sabine,
Welzel Peter
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1163::aid-ejoc1163>3.0.co;2-c
Subject(s) - chemistry , alkylation , salt (chemistry) , sodium salt , alkoxy group , organic chemistry , claisen rearrangement , stereochemistry , medicinal chemistry , alkyl , inorganic chemistry , catalysis
Abstract p ‐Alkoxy‐substituted cinnamylthiouronium salts 7 , 13 , 21a , and 21b reacted selectively with the 2‐acylamino‐1,3‐cyclopentanedione unit A of moenomycin A ( 1 ) to give the corresponding 2‐alkylated products 14a , 14b , 22a , and 22b . These products, depending on the pH of the solution, were either stable under the reaction conditions or they underwent retro‐Claisen‐type reactions. The method can be used for the attachment of reporter groups to moenomycin A for the synthesis of, for example, 25 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)