Organic Letters
Letter
(18) Fu, H.; Zhang, Y.; Wang, X.; Han, Y.; Peng, X.; Efferth, T.; Fu, Y.
Molecules 2014, 19, 17715.
(19) Ariamala, G.; Balasubramanian, K. K. Tetrahedron Lett. 1988, 29,
exploring for the preparation of other tetrahydrofuran-
containing natural products.
3335.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
(20) Bruns, A.; Wibbeling, B.; Frohlich, R.; Hoppe, D. Synthesis 2006,
2006, 3111.
(21) Feng, Z.-G.; Bai, W.-J.; Pettus, T. R. R. Angew. Chem., Int. Ed.
2015, 54, 1864.
(22) Cordigol was first isolated as an antifungal constituent of Cordia
goetzei Gurke by Hostettmann et al. in 1988,42 who tentatively assigned
it as having a trans-2,3-ring fusion by 1H NMR J value analysis. However,
the key coupling constants of its core are almost identical to those
reported for lophirone H. The cis-2,3-ring fusion in lophirone H was
established by NOESY in 1990,3 and in 1996 by Hostettmann et al.43
depicted cordigol as having the same relative stereochemistry as
lophirone H. This has become accepted.20,28,44,45
̈
̈
S
Full experimental details, copies of NMR spectra for all
new compounds, and links to the DFT calculations and
AUTHOR INFORMATION
■
Corresponding Author
ORCID
(23) Goel, A.; Kumar, A.; Raghuvanshi, A. Chem. Rev. 2013, 113, 1614.
́
(24) Jimenez-Gonzalez, L.; Alvarez-Corral, M.; Munoz-Dorado, M.;
́ ́
̃
Rodríguez-García, I. Phytochem. Rev. 2008, 7, 125.
(25) Rainier, J. D. In Synthesis of Saturated Oxygenated Heterocycles I,
Topics in Heterocyclic Chemistry 35; Cossy, J., Ed.; Springer: Berlin, 2014;
pp 1−41.
Author Contributions
†H.A. and S.M.L. contributed equally.
(26) Wolfe, J. P.; Hay, M. B. Tetrahedron 2007, 63, 261.
(27) Spivey, A. C.; Laraia, L.; Bayly, A. R.; Rzepa, H. S.; White, A. J. P.
Org. Lett. 2010, 12, 900.
Notes
(28) Zhao, L.-M.; Zhang, A.-L.; Gao, H.-S.; Zhang, J.-H. J. Org. Chem.
2015, 80, 10353.
The authors declare no competing financial interest.
(29) Abas, H.; Linsdall, S. M.; Mamboury, M.; Rzepa, H. S.; Spivey, A.
(30) Davies, S. G.; Sanganee, H. J. Tetrahedron: Asymmetry 1995, 6 (3),
671.
(31) Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron
Lett. 1986, 27, 4957.
(32) Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc.,
Perkin Trans. 1 1999, 387.
(33) Bull, S. D.; Davies, S. G.; Garner, A. C.; Kruchinin, D.; Key, M.-S.;
Roberts, P. M.; Savory, E. D.; Smith, A. D.; Thomson, J. E. Org. Biomol.
Chem. 2006, 4, 2945.
(34) Bunt, A. J.; Bailey, C. D.; Cons, B. D.; Edwards, S. J.; Elsworth, J.
D.; Pheko, T.; Willis, C. L. Angew. Chem., Int. Ed. 2012, 51, 3901.
(35) Willis et al.34 found that a para-phenolic styrenyl homoallylic
alcohol required an sulfonate protecting group to avoid polymerization
during a Lewis acid promoted 6-endo-trig oxonium−Prins reaction.
(36) At the outset, the choice of enantiomer was arbitrary since the
absolute configuration of natural (−)-lophirone H was unknown.
(37) Davies, S. G.; Elend, D. L.; Jones, S.; Roberts, P. M.; Savory, E. D.;
Smith, A. D.; Thomson, J. E. Tetrahedron 2009, 65, 7837.
(38) Aciro, C.; Steadman, V. A.; Pettit, S. N.; Poullennec, K. G.;
Lazarides, L.; Dean, D. K.; Dunbar, N. A.; Highton, A. J.; Keats, A. J.;
Siegel, D. S. WO2013185103A1, 2013.
ACKNOWLEDGMENTS
■
We thank Wang Hei (Elvis) Ng and Shuyue (Peter) Zhang
(Imperial College London) for preliminary experiments relating
to this synthesis.
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