Literature DB >> 17497871

Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction.

Yanxing Jia1, Michèle Bois-Choussy, Jieping Zhu.   

Abstract

Palladium-catalyzed intramolecular Suzuki-Miyaura reaction of linear tripeptide (23) afforded the 16-membered DEFG ring of complestatin (3) in good yield with an excellent atropdiastereoselectivity. Acidic treatment of 3 triggers a stereospecific rearrangement leading to the corresponding DEFG ring 4 of chloropeptin I.

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Year:  2007        PMID： 17497871     DOI： 10.1021/ol070889p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  A Pd(0)-mediated indole (macro)cyclization reaction.

Authors:  Steven P Breazzano; Yam B Poudel; Dale L Boger
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

2.  Total synthesis of complestatin: development of a Pd(0)-mediated indole annulation for macrocyclization.

Authors:  Hiroyuki Shimamura; Steven P Breazzano; Joie Garfunkle; F Scott Kimball; John D Trzupek; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

3.  Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.

Authors:  Chun-Ming Chio; Ying-Cheng Huang; You-Cheng Chou; Fu-Chun Hsu; Yen-Buo Lai; Chung-Shan Yu
Journal:  ACS Med Chem Lett       Date:  2020-03-16       Impact factor: 4.345

4.  Total synthesis of (+)-superstolide A.

Authors:  Mariola Tortosa; Neal A Yakelis; William R Roush
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

5.  Total synthesis of chloropeptin II (complestatin) and chloropeptin I.

Authors:  Joie Garfunkle; F Scott Kimball; John D Trzupek; Shinobu Takizawa; Hiroyuki Shimamura; Masaki Tomishima; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

6.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  6 in total

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