Total Synthesis and Structural Revision of Cyclotetrapeptide Asperterrestide A

Kosuke Ohsawa, Masato Sugai, Linnan Zhang, Yuichi Masuda, Masahito Yoshida, Takayuki Doi

Research output: Contribution to journalReview article

Abstract

The structural revision of cyclotetrapeptide asperterrestide A has been achieved based on total synthesis and molecular modeling. For these studies, (2R,3S)-MePhe(3-OH) and (2S,3S)-MePhe(3-OH) suitably protected for peptide synthesis were prepared via a stereoselective reduction of a ketone precursor derived from L-or d-serine, using L-selectride or DIBAL-H. The synthesis of the proposed structure of asperterrestide A (1a) was accomplished by solution-phase synthesis of a linear precursor followed by macrolactamization. The NMR spectra of our synthetic 1a were not identical to those reported for the natural compound. Molecular modeling studies suggested that the correct structure 1b was the one in which the stereochemistry at the α-positions of the Ala and MePhe(3-OH) residues is the opposite to that of the proposed structure. This was confirmed by the total synthesis of 1b and its subsequent structural characterization.

Original languageEnglish
Pages (from-to)6765-6779
Number of pages15
JournalJournal of Organic Chemistry
Volume84
Issue number11
DOIs
Publication statusPublished - 2019 Jun 7

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total Synthesis and Structural Revision of Cyclotetrapeptide Asperterrestide A'. Together they form a unique fingerprint.

  • Cite this