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Literature DB >> 33336547

Convergent Total Synthesis of Yaku'amide A.

Yu Cai¹, Zhiwei Ma¹, Jintao Jiang¹, Concordia C L Lo¹, Shi Luo¹, Ankur Jalan¹, Joseph M Cardon¹, Alexander Ramos¹, Diego A Moyá¹, Daniel Joaquin¹, Steven L Castle¹.

Abstract

Total synthesis of the anticancer peptide natural product yaku'amide A is reported. Its β-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E- and Z-ΔIle residues was accomplished through a one-pot reaction featuring anti dehydration, azide reduction, and O→N acyl transfer. Alkene isomerization was negligible during this process. These methods enabled a highly convergent and efficient synthetic route to the natural product.

Entities: Chemical

Keywords: O→N acyl transfer; aminohydroxylation; natural products; peptides; total synthesis

Mesh：

Substances：

Year: 2021 PMID： 33336547 PMCID： PMC7902439 DOI： 10.1002/anie.202014238

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

28 in total

1. Synthetic studies on thiostrepton: construction of thiostrepton analogues with the thiazoline-containing macrocycle.

Authors: K C Nicolaou; Marta Nevalainen; Mark Zak; Stephan Bulat; Marco Bella; Brian S Safina
Journal: Angew Chem Int Ed Engl Date: 2003-07-28 Impact factor: 15.336

2. Yaku'amides A and B, cytotoxic linear peptides rich in dehydroamino acids from the marine sponge Ceratopsion sp.

Authors: Reiko Ueoka; Yuji Ise; Susumu Ohtsuka; Shigeru Okada; Takao Yamori; Shigeki Matsunaga
Journal: J Am Chem Soc Date: 2010-12-01 Impact factor: 15.419

3. The enantioselective synthesis of phomopsin B.

Authors: Joshua S Grimley; Andrew M Sawayama; Hiroko Tanaka; Michelle M Stohlmeyer; Thomas F Woiwode; Thomas J Wandless
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Elucidation and Total Synthesis of the Correct Structures of Tridecapeptides Yaku'amides A and B. Synthesis-Driven Stereochemical Reassignment of Four Amino Acid Residues.

Authors: Takefumi Kuranaga; Hiroyuki Mutoh; Yusuke Sesoko; Tomomi Goto; Shigeki Matsunaga; Masayuki Inoue
Journal: J Am Chem Soc Date: 2015-07-17 Impact factor: 15.419

5. Target Identification of Yaku'amide B and Its Two Distinct Activities against Mitochondrial F_oF₁-ATP Synthase.

Authors: Kai Kitamura; Hiroaki Itoh; Kaori Sakurai; Shingo Dan; Masayuki Inoue
Journal: J Am Chem Soc Date: 2018-09-12 Impact factor: 15.419

6. Minor congeners of antrimycin: application of secondary ion mass spectrometry (SIMS) to structure determination.

Authors: K Morimoto; N Shimada; H Naganawa; T Takita; H Umezawa; H Kambara
Journal: J Antibiot (Tokyo) Date: 1982-03 Impact factor: 2.649

7. Stereoselective intermolecular C-H amination reactions.

Authors: Hélène Lebel; Carl Trudel; Cédric Spitz
Journal: Chem Commun (Camb) Date: 2012-06-29 Impact factor: 6.222

8. Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.

Authors: Jeffrey A Turk; Gonzalo S Visbal; Mark A Lipton
Journal: J Org Chem Date: 2003-10-03 Impact factor: 4.354

Convergent Total Synthesis of Yaku'amide A.

1. Synthetic studies on thiostrepton: construction of thiostrepton analogues with the thiazoline-containing macrocycle.

2. Yaku'amides A and B, cytotoxic linear peptides rich in dehydroamino acids from the marine sponge Ceratopsion sp.

3. The enantioselective synthesis of phomopsin B.

4. Elucidation and Total Synthesis of the Correct Structures of Tridecapeptides Yaku'amides A and B. Synthesis-Driven Stereochemical Reassignment of Four Amino Acid Residues.

5. Target Identification of Yaku'amide B and Its Two Distinct Activities against Mitochondrial F_oF₁-ATP Synthase.

6. Minor congeners of antrimycin: application of secondary ion mass spectrometry (SIMS) to structure determination.

7. Stereoselective intermolecular C-H amination reactions.

8. Asymmetric synthesis of four diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid: proof of configurational assignment.

9. Solid-Phase Total Synthesis of Yaku'amide B Enabled by Traceless Staudinger Ligation.

10. Total synthesis of celogentin C.

1. Synthesis and evaluation of potent yaku'amide A analogs.

2. Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates.

3. Towards a streamlined synthesis of peptides containing α,β-dehydroamino acids.