Highly stereoselective synthesis of α-hydroxy β-amino acids through β-lactams: application to the synthesis of the taxol and bestatin side chains and related systems.
Formation of α-hydroxy β-lactams, followed by chemical elaboration at C4 and further β-lactam cleavage afforded α-hydroxy β-amino acids or their derivatives in a highly stereoselective manner.
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Cited by (110)
Synthesis of β-lactams with π electron-withdrawing substituents
2012, TetrahedronCitation Excerpt :In 2000, Almqvist's group prepared various enantiopure 6-acylpenicillanic acid ethyl esters in satisfactory to good yields via reaction of 5-(1-hydroxyalkylidene)-1,3-dioxane-4,6-diones, tautomers of 5-acyl-1,3-dioxane-4,6-diones, and ethyl (R)-thiazoline-4-carboxylate in xylene in the presence of hydrogen chloride. The reaction produces trans-3-acyl-β-lactams as well (Scheme 46).34,35 It should be very useful method to synthesize trans-3-acyl-β-lactams.
Selectivities in the reaction of vicinal diimines and acyl chlorides
2011, TetrahedronCitation Excerpt :Both 4-imino-β-lactams and bis-β-lactams are important intermediates in organic and pharmaceutical chemistry.1,2 4-Imino-β-lactams can be converted to 4-acyl-β-lactams, which have been widely used in the synthesis of α-amino acid derivatives3,4 and β-amino acid derivatives5,6 via the ring-opening. They have also been applied in the preparation of heterocyclic compounds,7–25 alkaloids,23,26 antibiotics,27–31 even more complex natural products via the ring enlargement.23,32
Synthesis and bioactivity of a side chain bridged paclitaxel: A test of the T-Taxol conformation
2009, Bioorganic and Medicinal Chemistry LettersSemisynthesis of taxol and taxotere
2021, Taxol®: Science and Applications