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
. 2008 Jan 23;130(3):810-1.
doi: 10.1021/ja710294k. Epub 2007 Dec 29.

The catalytic asymmetric total synthesis of elatol

David E White  1 , Ian C Stewart, Robert H Grubbs, Brian M Stoltz
Affiliations

The catalytic asymmetric total synthesis of elatol

David E White et al. J Am Chem Soc. .

Abstract

Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Examples of chamigrene natural products.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
a dmdba = bis(3,5-dimethoxybenzylidene)acetone.
Scheme 3
Scheme 3
a Conditions: (a) HCO2H, Pd(OAc)2 (10 mol%), 18 (12.5 mol%), MS 4Å, benzene, 40 °C, (b) Pd(dmdba)2 (10 mol%), 18 (13 mol%), benzene, 40 °C.
Scheme 4
Scheme 4
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Erickson KL. Constituents of Laurencia. In: Scheuer PJ, editor. Marine Natural Products: Chemical and Biological Perspectives. V. Academic Press; New York: 1983. pp. 131–257.
    2. Dorta A, Díaz-Marrero AR, Cueto M, D’Croz L, Maté JL, Darias J. Tetrahedron Lett. 2004;45:7065–7068.

    1. Originally isolated from the marine alga Laurencia elata: Sims JJ, Lin GHY, Wing RM. Tetrahedron Lett. 1974;15:3487–3490.

    1. Granado I, Caballero P. Sci Mar. 1995;59(Supl 1):31–39.de Nys R, Leya T, Maximilien R, Afsar A, Nair PSR, Steinberg PD. Biofouling. 1996;10:213–224.Martín JD, Pérez C, Ravelo JL. J Am Chem Soc. 1986;108:7801–7811.Vairappan CS, Daitoh M, Suzuki M, Abe T, Masuda M. Phytochemistry. 2001;58:291–297.Vairappan CS. Biomol Eng. 2003;20:255–259.König GM, Wright AD. J Nat Prod. 1997;60:967–970.(g) HeLa: IC50 = 4.1 μM (lag phase), 1.3 μM (log phase); Hep-2: IC50 = 2.4 μM (lag phase), 2.0 μM (log phase); Dias T, Brito I, Moujir L, Paiz N, Darias J, Cueto M. J Nat Prod. 2005;68:1677–1679.

    1. For the preparation of elatol (1) via the degradation of isoobtusol, see: González AG, Darias J, Díaz A, Fourneron JD, Martín JD, Pérez C. Tetrahedron Lett. 1976;17:3051–3054.González AG, Martín JD, Martín VS, Martínez-Ripoll M, Fayos J. Tetrahedron Lett. 1979;20:2717–2718.González AG, Martín JD, Martín VS, Norte M, Pérez R. Tetrahedron Lett. 1982;23:2395–2398.

    1. For lead references on the total syntheses of other chamigrene natural products, see: Taber DF, Sikkander MI, Storck PH. J Org Chem. 2007;72:4098–4101.Srikrishna A, Lakshmi BV, Mathews M. Tetrahedron Lett. 2006;47:2103–2106.Chen YJ, Wang CY, Lin WY. Tetrahedron. 1996;52:13181–13188.Hatsui T, Wang JJ, Takeshita H. Bull Chem Soc Jpn. 1994;67:2507–2513. Also see ref 3c.

Publication types