Total synthesis of cyclodepsipeptide spiruchostatin A on silyl-linked polymer-support

Masahito Yoshida, Ken Ichi Sasahara, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Solid-phase total synthesis of cyclodepsipeptide spiruchostatin A (1) has been achieved. Initially, immobilization of the Boc-d-Val-statine derivative 3 via the hindered β-hydroxy group was efficiently achieved using polymer-supported silyl triflate. Subsequently, the peptide chain was successfully extended on the polymer-support to yield the tetrapeptide cyclization precursor 2 with high purity. 2-Methyl-6-nitrobenzoic anhydride (MNBA)-mediated macrolactonization of 2 proceeded smoothly on the polymer-support to provide macrolactone 12. Finally, release of the macrolactone from the polymer-support followed by in situ disulfide formation furnished spiruchostatin A (1) in 17% overall yield.

Original languageEnglish
Article number27009
Pages (from-to)7647-7653
Number of pages7
JournalTetrahedron
Volume71
Issue number40
DOIs
Publication statusPublished - 2015 Oct 7

Keywords

  • Cyclodepsipeptide
  • Histone deacetylase
  • Macrolactonization
  • Silyl linker
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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