1997
DOI: 10.1016/s0040-4039(97)01083-6
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Malic acid: A convenient precursor for the synthesis of peptide secondary structure mimetics

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Cited by 32 publications
(17 citation statements)
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“…Compound 26 was then oxidized to the aldehyde 27 . The C26–C35 side chain required for the construction of the complete lasonolide A skeleton was obtained as the phosphonium salt 30 from the known acetonide 28 14 and alcohol 29 15 by acid‐mediated esterification, followed by silylation and nucleophilic substitution with PPh 3 . The Wittig olefination of 27 and 30 was most effective in the presence of KHMDS, and the protected lasonolide A 31 was desilylated uneventfully to produce the natural (+)‐lasonolide A ( 1 ), all physical and spectroscopic data of which were identical to those reported in the literature 1.…”
Section: Methodsmentioning
confidence: 99%
“…Compound 26 was then oxidized to the aldehyde 27 . The C26–C35 side chain required for the construction of the complete lasonolide A skeleton was obtained as the phosphonium salt 30 from the known acetonide 28 14 and alcohol 29 15 by acid‐mediated esterification, followed by silylation and nucleophilic substitution with PPh 3 . The Wittig olefination of 27 and 30 was most effective in the presence of KHMDS, and the protected lasonolide A 31 was desilylated uneventfully to produce the natural (+)‐lasonolide A ( 1 ), all physical and spectroscopic data of which were identical to those reported in the literature 1.…”
Section: Methodsmentioning
confidence: 99%
“…Their reactions occur in mild conditions (0 C) with sulfonates prepared from a-hydroxy esters and with inversion of configuration (Scheme 2.4) [22,67,96,97]. Their reactions occur in mild conditions (0 C) with sulfonates prepared from a-hydroxy esters and with inversion of configuration (Scheme 2.4) [22,67,96,97].…”
Section: Reaction Of Hydrazine Derivatives With Enantiopure Activatedmentioning
confidence: 99%
“…The crystal structures of at least one simple dioxolanone derivative of (À)-malic acid is also known (Pang et al, 1997). For related literature, see: Green et al (1995); Kim et al (1997); Mulzer et al (2000); Ohfune et al (1981); Oida et al (1989); Shioiri et al (1995Shioiri et al ( , 1997; Stocksdale et al (2005).…”
Section: Related Literaturementioning
confidence: 99%
“…Acta Cryst. C41, 956-959. and unnatural synthetic targets (Green et al, 1995;Kim et al, 1997;Mulzer et al, 2000). The reported syntheses of many phytosiderophores and their analogs have utilized the title compound (I) (Ohfune et al, 1981;Shioiri et al, 1995;Shioiri et al, 1997).…”
Section: Tablementioning
confidence: 99%