Literature DB >> 29503022

Synthetic efforts towards the stereoselective synthesis of NF00659B1.

Do-Yeon Kwon1, Kiyoun Lee2, Hyeri Park1, Mi Jung Kim3, Jiyong Hong4.   

Abstract

NF00659B1 is a novel α-pyrone diterpenoid natural product with potent anti-colon cancer activity. A stereoselective approach to the 2,2-dimethyl oxepanol core of NF00659B1 is described enlisting a sequence of olefinic ester ring-closing metathesis, epoxidation, and Grignard addition. This strategy paves the way to a total synthesis of NF00659B1 for further biological studies.
Copyright © 2018 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Colon cancer; Dimethyl oxepanol; NF00659B(1); Natural products; Olefinic ester ring-closing metathesis; Pyrone diterpenoid

Mesh:

Substances:

Year:  2018        PMID: 29503022      PMCID: PMC6098985          DOI: 10.1016/j.bmcl.2018.02.038

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  26 in total

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3.  Sesquicillin, an inhibitor of glucocorticoid mediated signal transduction.

Authors:  L Engel; G Erkel; T Anke; O Sterner
Journal:  J Antibiot (Tokyo)       Date:  1998-05       Impact factor: 2.649

4.  Total synthesis of gambierol: subunit coupling and completion.

Authors:  Henry W B Johnson; Utpal Majumder; Jon D Rainier
Journal:  Chemistry       Date:  2006-02-08       Impact factor: 5.236

5.  Total synthesis, assignment of the absolute stereochemistry, and structure-activity relationship studies of subglutinols A and B.

Authors:  Hyoungsu Kim; Joseph B Baker; Yongho Park; Hyung-Bae Park; Patrick D DeArmond; Seong Hwan Kim; Michael C Fitzgerald; Dong-Sup Lee; Jiyong Hong
Journal:  Chem Asian J       Date:  2010-08-02

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Journal:  J Am Chem Soc       Date:  2011-02-15       Impact factor: 15.419

7.  Olefinic-lactone cyclizations to macrocycles.

Authors:  John C Rohanna; Jon D Rainier
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

8.  Two-directional olefinic-ester ring-closing metathesis using reduced Ti alkylidenes. A rapid entry into polycyclic ether skeletons.

Authors:  Yuan Zhang; Jon D Rainier
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  Synthesis of an A-E gambieric acid subunit with use of a C-glycoside centered strategy.

Authors:  Scott W Roberts; Jon D Rainier
Journal:  Org Lett       Date:  2007-05-01       Impact factor: 6.005

10.  Olefinic ester and diene ring-closing metathesis using a reduced titanium alkylidene.

Authors:  Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2007-09-27       Impact factor: 15.419

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