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Michigan Publishing, Arkivoc, 3(2010), p. 191-202, 2009

DOI: 10.3998/ark.5550190.0011.317

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Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

Journal article published in 2010 by Marta Perez-Fernandez, Alberto Avenoza, Jesus Héctor Busto ORCID, Jesus Manuel Peregrina ORCID, Fernando Rodriguez
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.