Natural Products
FULL PAPER
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Scheme 14. a) TPAP, NMO (90%); b) LiHMDS, NEt3, TMSCl; c) Pd-
(OAc)2, CH3CN, RT (90%, 2 steps); d) MeMgBr, ꢀ708C (94%); e)
TBSOTf, CH2Cl2, RT (96%); f) DDQ, CH2Cl2, H2O (98%); g) TPAP,
NMO, CH2Cl2; h) NaClO2, 2-methyl-2-butene, NaH2PO4, H2O, tBuOH
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a highly substituted oxepene using either the second genera-
tion Grubbs catalyst 38 or the Schrock catalyst 39. Equally
important to these fundamental issues is that the reactions
listed above have enabled us to generate sufficient quanti-
ties of the A–C and F–H substrates to complete our gam-
bierol efforts. This work is described in the accompanying
manuscript.
Acknowledgements
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We are grateful to the National Institutes of Health, General Medical
Sciences (GM56677) for support of this work. We would like to thank
Dr. Charles Mayne for help with NMR experiments and Dr. Elliot M.
Rachlin for help in obtaining mass spectra.
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Chem. Eur. J. 2006, 12, 1736 – 1746
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