First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A.

Authors :: Boyaud F
Mahiout Z
Lenoir C
Tang S
Wdzieczak-Bakala J
Witczak A
Bonnard I
Banaigs B
Ye T
Inguimbert N
Source :: Organic letters [Org Lett] 2013 Aug 02; Vol. 15 (15), pp. 3898-901. Date of Electronic Publication: 2013 Jul 15.
Publication Year :: 2013
Abstract: The first total synthesis of laxaphycin B was accomplished through stepwise automated Solid Phase Peptide Synthesis (SPPS), leading to the structural revision of its stereochemistry especially with regard to the configuration of one of the two 3-hydroxyleucines of this cyclic dodecapeptide of marine origin. The analogous Lyngbyacyclamide A was obtained by an extension of this synthesis.

Subjects :: Magnetic Resonance Spectroscopy
Molecular Structure
Peptides, Cyclic chemistry
Solid-Phase Synthesis Techniques
Stereoisomerism
Peptides, Cyclic chemical synthesis

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