Organic Letters
Letter
Scheme 2. Synthesis of Austrodoral and Austrodoric Acid
ACKNOWLEDGMENTS
This work was supported by the National Natural Science
Foundation of China (21672046, 21272046, and 21372054).
■
REFERENCES
■
(1) (a) Rao, H.; Li, C.-J. Angew. Chem., Int. Ed. 2011, 50, 8936.
(b) Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426. (c) Deng, K.;
Huai, Q.-Y.; Shen, Z.-L.; Li, H.-J.; Liu, C.; Wu, Y.-C. Org. Lett. 2015, 17,
1473. (d) Kotha, S.; Meshram, M.; Khedkar, P.; Banerjee, S.; Deodhar,
D. Beilstein J. Org. Chem. 2015, 11, 1833. (e) Li, H.-J.; Wang, R.; Gao, J.;
Wang, Y.-Y.; Luo, D.-H.; Wu, Y.-C. Adv. Synth. Catal. 2015, 357, 1393.
(f) West, T. H.; Spoehrle, S. S. M.; Kasten, K.; Taylor, J. E.; Smith, A. D.
ACS Catal. 2015, 5, 7446. (g) Ji, Y.-Z.; Wang, M.; Li, H.-J.; Liu, Y.; Wu,
Y.-C. Eur. J. Org. Chem. 2016, 2016, 4077. (h) Wu, H.; Yang, B.; Zhu, L.;
Lu, R.; Li, G.; Lu, H. Org. Lett. 2016, 18, 5804. (i) Wang, H.-S.; Li, H.-J.;
Wang, J.-L.; Wu, Y.-C. Green Chem. 2017, 19, 2140.
(2) For a seminal review, see: Song, Z. L.; Fan, C. A.; Tu, Y. Q. Chem.
Rev. 2011, 111, 7523.
(3) Gavagnin, M.; Carbone, M.; Mollo, E.; Cimino, G. Tetrahedron
Lett. 2003, 44, 1495.
Scheme 3. Synthesis of 8-epi-11-Nordriman-9-one and a
Formal Synthesis of Siphonodictyal B and Liphagal
(4) (a) Kulcitki, V.; Ungur, N.; Gavagnin, M.; Carbone, M.; Cimino, G.
Eur. J. Org. Chem. 2005, 2005, 1816. (b) Alvarez-Manzaneda, E. J.;
Chahboun, R.; Barranco, I.; Torres, E. C.; Alvarez, E.; Alvarez-
Manzaneda, R. Tetrahedron Lett. 2005, 46, 5321. (c) Alonso, P.;
Pardo, P.; Galvan, A.; Fananas, F. J.; Rodriguez, F. Angew. Chem., Int. Ed.
2015, 54, 15506. (d) Fujiwara, N.; Kinoshita, M.; Uchida, A.; Ono, M.;
Kato, K.; Akita, H. Chem. Pharm. Bull. 2012, 60, 562.
(5) (a) Chang, C. K.; Sotiriou, C. J. Heterocycl. Chem. 1985, 22, 1739.
(b) Depetris, G.; Giacomello, P.; Pizzabiocca, A.; Renzi, G.; Speranza,
M. J. Am. Chem. Soc. 1988, 110, 1098. (c) Nakamura, K.; Osamura, Y. J.
Am. Chem. Soc. 1993, 115, 9112. (d) Pandey, R. K.; Isaac, M.;
MacDonald, I.; Medforth, C. J.; Senge, M. O.; Dougherty, T. J.; Smith,
K. M. J. Org. Chem. 1997, 62, 1463. (e) Barili, P. L.; Berti, G.; Macchia,
B.; Macchia, F.; Monti, L. J. Chem. Soc. C 1970, 1168.
(6) Dastlik, K. A.; Ghisalberti, E. L.; Skelton, B. W.; White, A. H. Aust. J.
Chem. 1991, 44, 123.
(7) (a) Sullivan, B.; Djura, P.; McIntyre, D. E.; Faulkner, D. J.
Tetrahedron 1981, 37, 979. (b) Marion, F.; Williams, D. E.; Patrick, B.
O.; Hollander, I.; Mallon, R.; Kim, S. C.; Roll, D. M.; Feldberg, L.; Van
Soest, R.; Andersen, R. J. Org. Lett. 2006, 8, 321. (c) Chan, J. A.; Freyer,
A. J.; Carte, B. K.; Hemling, M. E.; Hofmann, G. A.; Mattern, M. R.;
Mentzer, M. A.; Westley, J. W. J. Nat. Prod. 1994, 57, 1543. (d) Grube,
A.; Assmann, M.; Lichte, E.; Sasse, F.; Pawlik, J. R.; Kock, M. J. Nat. Prod.
2007, 70, 504. (e) Kim, J. W.; Ko, S. K.; Kim, H. M.; Kim, G. H.; Son, S.;
Kim, G. S.; Hwang, G. J.; Jeon, E. S.; Shin, K. S.; Ryoo, I. J.; Hong, Y. S.;
Oh, H.; Lee, K. H.; Soung, N. K.; Hashizume, D.; Nogawa, T.;
Takahashi, S.; Kim, B. Y.; Osada, H.; Jang, J. H.; Ahn, J. S. J. Nat. Prod.
2016, 79, 2703. (f) Ayer, W. A.; Miao, S. Can. J. Chem. 1993, 493 (71),
487. (g) Ma, X.; Li, L.; Zhu, T.; Ba, M.; Li, G.; Gu, Q.; Guo, Y.; Li, D. J.
Nat. Prod. 2013, 76, 2298.
(8) Nakamura, K.; Osamura, Y. J. Phys. Org. Chem. 1990, 3, 737.
(9) (a) Montenegro, I.; Pino, L.; Werner, E.; Madrid, A.; Espinoza, L.;
Moreno, L.; Villena, J.; Cuellar, M. Molecules 2013, 18, 4192.
(b) Quideau, S.; Lebon, M.; Lamidey, A. M. Org. Lett. 2002, 4, 3975.
(10) Margaros, I.; Montagnon, T.; Vassilikogiannakis, G. Org. Lett.
2007, 9, 5585.
regioselectivity, a wide substrate scope, short reaction times, and
mild reaction conditions. Our endeavors will lead to a better
understanding of the controlling elements behind their structural
motifs. Further applications of this regioselective 1,2-diol
rearrangement for the diversity-oriented synthesis of other
natural products with related skeletons are currently under
investigation, and will be reported in due course.
ASSOCIATED CONTENT
■
S
* Supporting Information
The Supporting Information is available free of charge on the
General experimental procedure and characterization data
(11) Dixon, D. D.; Lockner, J. W.; Zhou, Q.; Baran, P. S. J. Am. Chem.
Soc. 2012, 134, 8432.
(12) (a) Vlad, P. F.; Aryku, A. N.; Chokyrian, A. G. Russ. Chem. Bull.
2004, 53, 443. (b) Vlad, P. F.; Kuchkova, K. I.; Aryku, A. N.; Deleanu, K.
Russ. Chem. Bull. 2005, 54, 2656.
(13) (a) Kluge, A. F.; Cloudsdale, I. S. J. Org. Chem. 1979, 44, 4847.
(b) Anderson, J. C.; Cornell, A. C.; Timothy; Hodgkinson, J.; Wilkinson,
J. A. Synth. Commun. 2001, 31, 939.
(14) Markwell-Heys, A. W.; Kuan, K. K. W.; George, J. H. Org. Lett.
2015, 17, 4228.
AUTHOR INFORMATION
■
Corresponding Authors
ORCID
Notes
The authors declare no competing financial interest.
D
Org. Lett. XXXX, XXX, XXX−XXX