Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Sep 3;12(17):3752-5.
doi: 10.1021/ol101340n.

Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence

Dong Gao  1 , George A O'Doherty
Affiliations

Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence

Dong Gao et al. Org Lett. .

Abstract

A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Fostriecin (1, CI-920)
Figure 2
Figure 2
Related natural products to fostriecin
Scheme 1
Scheme 1
Fostriecin (1) retrosynthesis
Scheme 2
Scheme 2
Synthesis of trieneoate 10
Scheme 3
Scheme 3
Asymmetric hydration and oxidation of triene 10
Scheme 4
Scheme 4
Substrate optimization for the trans-hydroboration
Scheme 5
Scheme 5
Trans-hydroboration and pyranone installation
Scheme 6
Scheme 6
Fostriecin End-Game
See this image and copyright information in PMC

References

    1. Tunac JB, Graham BD, Dobson WE. J. Antibiot. 1983;36:1595. - PubMed
    2. Stampwala SS, Bunge RH, Hurley TR, Wilmer NE, Brankiewicz AJ, Steinman CE, Smitka TA, French JC. J. Antibiot. 1983;36:1601. - PubMed
    3. Hokanson GC, French JC. J. Org. Chem. 1985;50:462.
    1. Lewy DS, Gauss C-M, Soenen DR, Boger DL. Curr. Med. Chem. 2002;9:2005. - PubMed
    2. De Jong RS, De Vries EGE, Mulder NH. Anti- Cancer Drugs. 1997;8:413. - PubMed

    1. Reviews: Jackson RC, Fry DW, Boritzki TJ, Roberts BJ, Hook KE, Leopold WR. Adv. Enzyme Regul. 1985;23:193. Scheithauer W, Hoff DDV, Clark GM, Shillis JL, Elslager EF. Eur. J. Clin. Oncol. 1986;22:921.

    1. Reviews: Walsh AH, Cheng A, Honkanen RE. FEBS Lett. 1997;416:230. Hastie CJ, Cohen PTW. FEBS Lett. 1998;431:357.

    1. Boger DL, Hikota M, Lewis BM. J. Org. Chem. 1997;62:1748.

Publication types