Synthetic efforts towards the stereoselective synthesis of NF00659B1

Do-Yeon Kwon; Kiyoun Lee; Hyeri Park; Mi Jung Kim; Jiyong Hong

doi:10.1016/j.bmcl.2018.02.038

Synthetic efforts towards the stereoselective synthesis of NF00659B₁

Bioorg Med Chem Lett. 2018 Sep 1;28(16):2746-2750. doi: 10.1016/j.bmcl.2018.02.038. Epub 2018 Feb 19.

Authors

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

Affiliations

¹ Department of Chemistry, Duke University, Durham, NC 27708, United States.
² Department of Chemistry, The Catholic University of Korea, Bucheon 14662, Republic of Korea.
³ Korea Research Institute of Bioscience and Biotechnology, Daejeon 34141, Republic of Korea.
⁴ Department of Chemistry, Duke University, Durham, NC 27708, United States. Electronic address: [email protected].

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.

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

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Molecular Conformation
Stereoisomerism

Substances

Alkenes
Biological Products

Grants and funding

R21 AI128283/AI/NIAID NIH HHS/United States