Literature DB >> 33994597

Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline.

Byron A Boon1, Yi-Yun Yu1, Dale L Boger1.   

Abstract

A concise total synthesis of (-)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4+2]/[3+2] cycloaddition cascade that formed four C-C bonds, created three new rings, and established five contiguous stereocenters about the new formed central 6-membered ring.

Entities:  

Keywords:  Vinca alkaloids; oxadiazole cycloaddition cascade; vindoline analogue

Year:  2021        PMID： 33994597      PMCID： PMC8117404          DOI： 10.1016/j.tet.2021.132117

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  35 in total

1.  Total synthesis of (-)- and ent-(+)-vindoline.

Authors:  Younggi Choi; Hayato Ishikawa; Juraj Velcicky; Gregory I Elliott; Michael M Miller; Dale L Boger
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

2.  Asymmetric total synthesis of vindoline.

Authors:  Daisuke Kato; Yoshikazu Sasaki; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

3.  Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Authors:  Annie Tam; Hiroaki Gotoh; William M Robertson; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-09-19       Impact factor: 2.823

4.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

5.  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors:  Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal:  J Med Chem       Date:  2013-01-04       Impact factor: 7.446

6.  A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.

Authors:  Erick K Leggans; Katharine K Duncan; Timothy J Barker; Kristin D Schleicher; Dale L Boger
Journal:  J Med Chem       Date:  2012-12-17       Impact factor: 7.446

7.  Differential activity of vincristine and vinblastine against cultured cells.

Authors:  P J Ferguson; J R Phillips; M Selner; C E Cass
Journal:  Cancer Res       Date:  1984-08       Impact factor: 12.701

8.  Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2016-01-27       Impact factor: 22.384

9.  Interaction of vinca alkaloids with tubulin: a comparison of vinblastine, vincristine, and vinorelbine.

Authors:  S Lobert; B Vulevic; J J Correia
Journal:  Biochemistry       Date:  1996-05-28       Impact factor: 3.162

10.  Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity.

Authors:  Shouliang Yang; Kuppusamy Sankar; Colin K Skepper; Timothy J Barker; John C Lukesh; Daniel M Brody; Manuela M Brütsch; Dale L Boger
Journal:  Chem Sci       Date:  2016-11-03       Impact factor: 9.825
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