Total synthesis and configurational assignment of chondramide A

Anke Schmauder, L. David Sibley, Martin E. Maier

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

The first total synthesis of the cyclodepsipeptide chondramide A (2b) is described. This depsipeptide is composed of four subunits, namely Lalanine, N-Me-D-tryptophan, 3-amino-2-methoxy-propionic acid (β-tyrosine derivative), and a 7-hydroxy-alkenoic acid. While the configuration of the stereogenic centers in the 7-hydroxy-alkenoic acid were known, the configuration of the tyrosine derivative required clarification and turned out to be (2S,3R) or (2L,3L), respectively. The synthesis of the 3-amino-2-methoxy-3-arylpropanoic ester 20 b relied on an asymmetric dihydroxylation yielding diol ent-15a followed by a regioselective Mitsunobu substitution leading to 3-azido-2-hydroxypropanoate 18 b. We could also show that the ester bond in the seco compound 26b can be fashioned by a Mitsunobu esterification by using hydroxy ester (7S)-7 and the tripeptide acid 25 b. This synthesis should allow for the preparation of various analogues.

Original languageEnglish
Pages (from-to)4328-4336
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number14
DOIs
StatePublished - Apr 12 2010

Keywords

  • Amino acids
  • Asymmetric synthesis
  • Cyclodepsipeptides
  • Natural products
  • Peptides

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