Literature DB >> 27019081

Stereoselective Total Synthesis of (-)-Renieramycin T.

Masashi Yokoya1, Ryoko Toyoshima1, Toshihiro Suzuki1, Vy H Le2,3, Robert M Williams2,3, Naoki Saito1.   

Abstract

A stereoselective total synthesis of (-)-Renieramycin T (1t) from a key tetrahydroisoquinoline intermediate previously utilized in our formal total synthesis of Ecteinascidin 743 is described. The synthesis features a concise approach for construction of the pentacyclic framework using a Pictet-Spengler cyclization of bromo-substituted carbinolamine 17, which obviates the regioselectivity problem of the Pictet-Spengler cyclization. The results of cytotoxicity studies are also presented.

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Year:  2016        PMID: 27019081     DOI: 10.1021/acs.joc.6b00327

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  5-O-(N-Boc-l-Alanine)-Renieramycin T Induces Cancer Stem Cell Apoptosis via Targeting Akt Signaling.

Authors:  Darinthip Suksamai; Satapat Racha; Nicharat Sriratanasak; Chatchai Chaotham; Kanokpol Aphicho; Aye Chan Khine Lin; Chaisak Chansriniyom; Khanit Suwanborirux; Supakarn Chamni; Pithi Chanvorachote
Journal:  Mar Drugs       Date:  2022-03-29       Impact factor: 6.085

2.  Construction of the Pentacyclic Core and Formal Total Synthesis of (rac)-Renieramycin T.

Authors:  Shinya Kimura; Naoki Saito
Journal:  ChemistryOpen       Date:  2018-08-07       Impact factor: 2.911

3.  Structure-Activity Relationships and Molecular Docking Analysis of Mcl-1 Targeting Renieramycin T Analogues in Patient-derived Lung Cancer Cells.

Authors:  Korrakod Petsri; Masashi Yokoya; Sucharat Tungsukruthai; Thanyada Rungrotmongkol; Bodee Nutho; Chanida Vinayanuwattikun; Naoki Saito; Matsubara Takehiro; Ryo Sato; Pithi Chanvorachote
Journal:  Cancers (Basel)       Date:  2020-04-03       Impact factor: 6.639

  3 in total

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