Organic Letters
Letter
Scheme 3. Synthesis of (−)-Goniomitine
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corresponding reaction mixture with HOAc/THF/H2O
furnished the natural product (−)-goniomitine in one step in
60% yield. All the spectroscopic data of 1 were in agreement
with those of natural and synthetic goniomitine reported in the
literatue.2−8
In summary, we have accomplished the total synthesis of
natural product (−)-goniomitine in 11 linear steps starting
from commercially available diethyl L-malate. The synthesis
features a straightforward chiral pool approach to prepare the
chiral moiety, a highly efficient Ir-catalyzed C−H borylation to
synthesize the 2-indoleboronic acid pinacol ester, and a Suzuki
reaction to couple the two key intermediates. Notably, the high
degree of convergence of this strategy makes it particularly
amenable to the total synthesis of other members of the
aspidosperma family of natural products.
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ASSOCIATED CONTENT
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S
* Supporting Information
Full experimental procedures, and 1H and 13C NMR spectra of
compounds 1, 4−7, 10, 12, 15−19. This material is available
AUTHOR INFORMATION
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Corresponding Author
Notes
(21) Sparks, S. M.; Gutierrez, A. J.; Shea, K. J. J. Org. Chem. 2003, 68,
5274−5285.
(22) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.;
Meneses, R.; Romera, J. L. Synlett 2001, 485−488.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This research was supported by the National Natural Science
Foundation of China (Nos. 21372017, 21290183), the National
Basic Research Program of China (973 Program, NO.
2010CB833200), and NCET.
C
dx.doi.org/10.1021/ol501341b | Org. Lett. XXXX, XXX, XXX−XXX