Organic Letters
Letter
from this building block in two steps and a total yield of 37%
without the use of expensive olivetol. (−)-Δ -THC triflate can
also be used in carbonylative Stille reactions to access benzoyl-
substituted THC analogues. Importantly, no protecting groups
are needed for the synthesis of our building block and for all
investigated follow-up reactions.
(e) Shultz, Z. P.; Lawrence, G. A.; Jacobson, J. M.; Cruz, E. J.; Leahy,
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ASSOCIATED CONTENT
Supporting Information
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6062. (f) Razdan, R. K.; Handrick, G. R.; Dalzell, H. C. Experientia
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975, 31, 16−17.
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11) Westphal, M. V.; Schafroth, M. A.; Sarott, R. C.; Imhof, M. A.;
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1
3
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C spectra, and X-ray data (PDF)
Bold, C. P.; Leippe, P.; Dhopeshwarkar, A.; Grandner, J. M.; Katritch,
V.; Mackie, K.; Trauner, D.; Carreira, E. M.; Frank, J. A. J. Am. Chem.
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CCDC 1883131 contains the supplementary crystallographic
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
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AUTHOR INFORMATION
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ORCID
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Notes
Tius, M. A.; Thakur, G. A.; Bowman, A.; Wood, J. T.; Makriyannis, A.
J. Med. Chem. 2010, 53, 5656−5666.
(19) Molander, G. A.; Petrillo, D. E.; Landzberg, N. R.; Rohanna, J.
The authors declare no competing financial interest.
C.; Biolatto, B. Synlett 2005, 11, 1763−1766.
(20) Papahatjis, D. P.; Kourouli, T.; Abadji, V.; Goutopoulos, A.;
ACKNOWLEDGMENTS
This work was financially supported by the Deutsche
Forschungsgemeinschaft (DFG). We thank Prof. Erick
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Makriyannis, A. J. Med. Chem. 1998, 41, 1195−1200.
(21) Krishnamurthy, M.; Ferreira, A. M.; Moore, B. M., II Bioorg.
Med. Chem. Lett. 2003, 13, 3487−3490.
Carreira (ETH Zurich) for alluding to the problem concerning
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the regiochemistry of (−)-Δ -Br-THC.
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