A method for the introduction of reporter groups into moenomycin A, based on thiouronium salt chemistry
A Buchynskyy, K Stembera, L Hennig… - European Journal of …, 2002 - Wiley Online Library
A Buchynskyy, K Stembera, L Hennig, M Findeisen, S Giesa, P Welzel
European Journal of Organic Chemistry, 2002•Wiley Online LibraryAbstract 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 …
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 …
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)
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