Organic Letters
Letter
68, 3179. (f) Mohapatra, D. K.; Krishnarao, P. S.; Bhimireddy, E.;
Yadav, J. S. Synthesis 2014, 46, 1639.
of the synthetic isomers of cryptorigidifoliol K and the isolated
natural product, particularly with respect to the hydroxyl group
position, suggests that the structure proposed for the natural
product needs revision.
(4) (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N.
Science 1997, 277, 936. (b) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.;
Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen,
E. N. J. Am. Chem. Soc. 2002, 124, 1307. (c) Mori, K.; Shikichi, Y.;
Shankar, S.; Yew, J. Y. Tetrahedron 2010, 66, 7161.
ASSOCIATED CONTENT
* Supporting Information
■
S
(5) Mohapatra, D. K.; Das, P. P.; Pattanayak, M. R.; Yadav, J. S.
Chem. - Eur. J. 2010, 16, 2072.
The Supporting Information is available free of charge on the
(6) (a) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu,
O. Tetrahedron 1986, 42, 3021. (b) Shin, I.; Hong, S.; Krische, M. J. J.
Am. Chem. Soc. 2016, 138, 14246.
(7) (a) Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1999, 64, 293.
(b) Huang, L.; Teumelsan, N.; Huang, X. Chem. - Eur. J. 2006, 12,
5246.
Experimental procedure and characterization of new
compounds (1H, 13C NMR spectra, 2D NMR spectra)-
(8) Davies, S. G.; Fletcher, A. M.; Lee, J. A.; Roberts, P. M.; Russell,
A. J.; Taylor, R. J.; Thomson, A. D.; Thomson, J. E. Org. Lett. 2012, 14,
1672.
(9) (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin
Trans. 1 1975, 1574. (b) Barton, D. H. R.; Hartwig, W.; Motherwell,
R. S. H.; Motherwell, W. B.; Stange, A. Tetrahedron Lett. 1982, 23,
2019.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
(10) (a) Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8,
5481. (b) Seden, P. T.; Charmant, J. P. H.; Willis, C. L. Org. Lett.
2008, 10, 1637. (c) Yang, Z.; Zhang, B.; Zhao, G.; Yang, J.; Xie, X.;
She, X. Org. Lett. 2011, 13, 5916. (d) Reddy, D. S.; Padhi, B.;
Mohapatra, D. K. J. Org. Chem. 2015, 80, 1365.
(11) Zhang, Y.-Y.; Zhang, X.-H.; Wei, R.-J.; Du, B.-Y.; Fan, Z.-Q.; Qi,
G.-R. RSC Adv. 2014, 4, 36183.
(12) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.;
Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am.
Chem. Soc. 2002, 124, 1307.
(13) Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
(14) (a) Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170. (b) El
Fangour, S.; Guy, A.; Vidal, J.-P.; Rossi, J.-C.; Durand, T. J. Org. Chem.
2005, 70, 989. (c) Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.;
Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284.
(15) (a) Ohtani, I.; Kusumi, J.; Kashman, Y.; Kakisawa, H. J. Am.
Chem. Soc. 1991, 113, 4092. (b) Yoshida, W. Y.; Bryan, P. J.; Baker, B.
J.; McClintock, J. B. J. Org. Chem. 1995, 60, 780.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank the Council of Scientific and Industrial Research
(CSIR), New Delhi, India, for financial support as part of the
XII Five Year plan programme under the title ORIGIN (CSC-
0108). G.S.R., B.P., and Y.B. thank CSIR and UGC, New Delhi,
India, for financial assistance in the form of fellowships.
DEDICATION
■
This manuscript is dedicated to Dr. Mukund K. Gurjar, CSO,
Emcure Pharmaceuticals Pvt., Ltd., on the occasion of his 65th
birthday.
(16) Manikanta, G.; Nagaraju, T.; Radha Krishna, P. Synthesis 2016,
48, 4213.
(17) (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J.
Am. Chem. Soc. 2000, 122, 8168. (b) Chatterjee, A. K.; Sanders, D. P.;
Grubbs, R. H. Org. Lett. 2002, 4, 1939. (c) Chatterjee, A. K.; Choi, T.-
L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
REFERENCES
■
(1) (a) Rali, T.; Wossa, S. W.; Leach, D. N. Molecules 2007, 12, 149.
(b) Cardona, W.; Quinones, W.; Robledo, S.; Velez, I. D.; Murga, J.;
Garcia-Fortanet, J.; Carda, M.; Cardona, D.; Echeverri, F. Tetrahedron
2006, 62, 4086. (c) Sturgeon, C. M.; Cinel, B.; Diaz-Marrero, A. R.;
McHardy, L. M.; Ngo, M.; Andersen, R. J.; Roberge, M. Cancer
Chemother. Pharmacol. 2008, 61, 407. (d) Meragelman, T. L.;
Scudiero, D. A.; Davis, R. E.; Staudt, L. M.; McCloud, T. G.;
Cardellina, J. H.; Shoemaker, R. H. J. Nat. Prod. 2009, 72, 336.
(e) Grkovic, T.; Blees, J. S.; Colburn, N. H.; Schmid, T.; Thomas, C.
L.; Henrich, C. J.; McMahon, J. B.; Gustafson, K. R. J. Nat. Prod. 2011,
74, 1015. (f) Cuccarese, M. F.; Wang, Y.; Beuning, P. J.; O’Doherty, G.
A. ACS Med. Chem. Lett. 2014, 5, 522. (g) Toneto Novaes, L. F.;
Drekener, R. L.; Avila, C. M.; Pilli, R. A. Tetrahedron 2014, 70, 6467.
(h) Liu, Y.; Rakotondraibe, L. H.; Brodie, P. J.; Wiley, J. D.; Cassera,
M. B.; Miller, J. S.; Ratovoson, F.; Rakotobe, E.; Rasamison, V. E.;
Kingston, D. G. I. J. Nat. Prod. 2015, 78, 1330.
(2) (a) Smith, C. M.; O’Doherty, G. A. Org. Lett. 2003, 5, 1959.
(b) Tosaki, S.; Horiuchi, Y.; Nemoto, T.; Ohshima, T.; Shibasaki, M.
Chem. - Eur. J. 2004, 10, 1527. (c) Wang, X.; Wang, W.; Zheng, H.; Su,
Y.; Jiang, T.; He, Y.; She, X. Org. Lett. 2009, 11, 3136. (d) Mohapatra,
D. K.; Bhimireddy, E.; Krishnarao, P. S.; Das, P. P.; Yadav, J. S. Org.
Lett. 2011, 13, 744. (e) Albury, A. M. M.; Jennings, M. P. J. Org. Chem.
2012, 77, 6929.
(3) (a) Menz, H.; Kirsch, S. F. Org. Lett. 2009, 11, 5634. (b) Yadav, J.
S.; Rajendar, G.; Ganganna, B.; Srihari, P. Tetrahedron Lett. 2010, 51,
2154. (c) Ghosh, S.; Rao, C. N. Tetrahedron Lett. 2010, 51, 2052.
(d) Yadav, J. S.; Rajendar, G. Eur. J. Org. Chem. 2011, 2011, 6781.
(e) Kumaraswamy, G.; Murthy, A. N.; Sadaiah, K. Tetrahedron 2012,
D
Org. Lett. XXXX, XXX, XXX−XXX