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):3890-3.
doi: 10.1021/ol1015898.

Synthesis of the bis-tetrahydropyran core of amphidinol 3

Michael T Crimmins  1 , Timothy J Martin, Theodore A Martinot
Affiliations

Synthesis of the bis-tetrahydropyran core of amphidinol 3

Michael T Crimmins et al. Org Lett. .

Abstract

A convergent synthesis of the C31-C52 bis-tetrahydropyran core of the natural product amphidinol 3 is reported. A common intermediate was synthesized from d-tartaric acid utilizing an asymmetric glycolate alkylation/ring-closing metathesis sequence to construct the THP rings. Differential elaboration of the common intermediate allowed the synthesis of two distinct coupling partners which were joined through a modified Horner-Wadsworth-Emmons olefination to provide the bis-tetrahydropyran core.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis
Scheme 2
Scheme 2
Synthesis of Tetrahydropyran 5 and Elaboration to β-ketophosphonate 3
Scheme 3
Scheme 3
Synthesis of Aldehyde 4 and Fragment Coupling
See this image and copyright information in PMC

References

    1. Satake M, Murata M, Yasumoto T, Fujita T, Naoki H. J Am Chem Soc. 1991;113:9859–9861.
    1. Paul GK, Matsumori N, Konoki K, Sasaki M, Murata M, Tachibana K. Harmful and Toxic Algal Blooms
    1. Murata M, Matsuoka S, Matsumori N, Paul GK, Tachibana K. J Am Chem Soc. 1999;121:870.
    1. Oishi T, Kanemoto M, Swasono R, Matsumori N, Murata M. Org Lett. 2008;10:5203–5206. - PubMed
    1. BouzBouz S, Cossy J. Org Lett. 2001;3:1451–1454. - PubMed
    2. Cossy J, Tsuchiya T, Ferrie L, Reymond S, Kreuzer T, Colobert F, Jourdain P, Marko IE. Synlett. 2007:2286–2288.
    3. Colobert F, Kreuzer T, Cossy J, Reymond S, Tsuchiya T, Ferrie L, Marko IE, Jourdain P. Synlett. 2007:2351–2354.

Publication types