Asymmetric Synthesis of the C(17)–C(28) Subunit of Didemnaketal B
Xue-Qiang Li
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Department of Chemistry and the Key Laboratory of Natural Gas Conversion, Ningxia University, Yinchuan, Ningxia 750021, China
Search for more papers by this authorQin He
West China School of Pharmacy, Sichuan University, Chengdu, Sichuan 610000, China
Search for more papers by this authorFu-Min Zhang
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorShu-Yu Zhang
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorXue-Qiang Li
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Department of Chemistry and the Key Laboratory of Natural Gas Conversion, Ningxia University, Yinchuan, Ningxia 750021, China
Search for more papers by this authorQin He
West China School of Pharmacy, Sichuan University, Chengdu, Sichuan 610000, China
Search for more papers by this authorFu-Min Zhang
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorShu-Yu Zhang
Department of Chemistry and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China
Search for more papers by this authorAbstract
The stereocontrolled synthesis of the C(17)–C(28) fragment 3 of didemnaketal B was accomplished in 21 steps from the natural (R)-(+)-pulegone and (S)-(−)-citronellal. The key steps involved diastereoselective construction of two chiral carbon centers through the intramolecular chiral induction and uncommon Julia olefination of ketone forming the E-trisubstituted C(22)–C(23) double bound.
REFERENCES
- 1a Potts, B. C. M.; Faulkner, D. J.; Chan, J. A.; Simolike, G. C.; Offen, P.; Hhemling, M. E.; Francis, T. A.. J. Am. Chem. Soc., 1991, 113, 6321.
- 1b Pinka, J.; Faulkner, D.. Nat. Prod. Lett., 1995, 7, 291.
- 1c Fan, X. D.; Flentke, G. R.; Rich, D. H.. J. Am. Chem. Soc., 1998, 120, 8893.
- 2a Jia, Y. X.; Wu, B.; Li, X.; Ren, S. K.; Tu, Y. Q.; Chan, A. S. C.; Kitching, W.. Org. Lett., 2001, 3(6), 847.
- 2b Jia, Y. X.; Li, X.; Wu, B.; Zhao, X. Z.; Tu, Y. Q.. Tetrahedron, 2002, 58, 1697.
- 3 Salomon, C. E.; Williams, D. H.; Lobkovsky, E.; Clardy, J. C.; Faulkner, D. J.. Org. Lett., 2002, 4, 1699.
- 4a
Stemke, J. E.;
Chamberlin, A. R.;
Bond, F. T..
Tetrahedron Lett.,
1976,
17,
2947.
10.1016/S0040-4039(01)85496-4 Google Scholar
- 4b Silvestri, M. G.. J. Org. Chem., 1983, 48, 2419.
- 4c
Stemke, J. E.;
Bond, F. T..
Tetrahedron Lett.,
1975,
16,
1815.
10.1016/S0040-4039(00)75264-6 Google Scholar
- 4d
Shapiro, R. H.;
Lipton, M. F.;
Kolonko, K. J.;
Buswell, R. L.;
Capuano, L. A..
Tetrahedron Lett.,
1975,
16,
1811.
10.1016/S0040-4039(00)75263-4 Google Scholar
- 5a Sha, C. K.; Chiu, R. T.; Yang, C. F.; Yao, N. T.; Tseng, W. H.; Liao, F. L.; Wang, S. L.. J. Am. Chem. Soc., 1997, 119, 4130.
- 5b Dunlap, N. K.; Sabol, M. R.; Watt, D. S.. Tetrahedron Lett., 1984, 25, 5839.
- 5c Liao, X.; Wu, Y.; Brabander, J. K. D.. Angew. Chem., Int. Ed., 2003, 42, 1648.
- 6 Martin, S. F.; Ddge, J. A.. Tetrahedron Lett., 1991, 32, 3017.
- 7a Corey, E. J.; Venkateswarlu, A. E.. J. Am. Chem. Soc., 1972, 94, 6190.
- 7b Marshall, J. A.; Grote, J.; Audia, J. E.. J. Am. Chem. Soc., 1987, 109, 1186.
- 7c Shi, L.; Xia, W. J.; Zhang, F. M.; Tu, Y. Q.. Synlett, 2002, 1505.
- 7d Li, X. Q.; Zhao, X. Z.; Liu, P. N.; Tu, Y. Q.. Chin. Chem. Lett., 2004, 15, 757.
- 8a Yamada, S.; Morizon, D.; Yamamoto, K.. Tetrahedron Lett., 1992, 33, 4329.
- 8b
Hoffimann, R. W.;
Schlapbach, A..
Tetrahedron Lett.,
1993,
34,
7903.
10.1016/S0040-4039(00)61506-X Google Scholar
- 9a Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R.. J. Org. Chem., 1993, 58, 832.
- 9b Posner, G. H.; Switzer, C.. J. Am. Chem. Soc., 1986, 108, 1239.
- 9c Imperiali, B.; Roy, R. S.. J. Org. Chem., 1995, 60, 1891.
- 9d Wooley, K. L.; Hawker, C. J.; Frechet, M. J.. J. Am. Chem. Soc., 1991, 113, 4252.
- 10a Millar, J. G.; Underhill, E. W.. J. Org. Chem., 1986, 51, 4726.
- 10b Joseph, R.; Pallan, P. S.; Sudalai, A.; Ravindranathan, T.. Tetrahedron Lett., 1995, 36, 609.
- 10c Smith, A. B.; Barbosa, J.; Wang, W. C.; Wood, J. L.. J. Am. Chem. Soc., 1996, 118, 8316.
- 11a Evans, D. E.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M.. J. Am. Chem. Soc., 1999, 121, 7540.
- 11b Charette, A. B.; Lebel, H.. J. Am. Chem. Soc., 1996, 118, 10327.
- 11c Smith, A. B.; Barbosa, J.; Wang, W. C.; Wood, J. L.. J. Am. Chem. Soc., 1996, 118, 8316.
- 11d Carter, R. G.; Bourland, T. C.; Graves, D. E.. Org. Lett., 2002, 4, 2177.
- 12a Surprenant, S.; Chan, W. Y.; Berthelette, C.. Org. Lett., 2003, 5, 4851.
- 12b Ono, K.; Yoshida, A.; Saito, N.; Fujishima, T.; Honzawa, S.; Suhara, Y.; Kishimoto, S.; Sugiura, T.; Waku, K.; Takayama, H.; Kittaka, A.. J. Org. Chem., 2003, 68, 7407.
- 13a Poupon, J. C.; Demont, E.; Prunet, J.; Ferezou, J. P.. J. Org. Chem., 2003, 68, 4700.
- 13b Metternich, R.; Denni, D.; Thai, B.; Sedrani, R.. J. Org. Chem., 1999, 64, 9632.
- 14 Atsuya, K.; Zheng, B. Z.; Kusaka, S. I.; Kuroda, M.; Yoshimoto, K.; Yamada, H.; Yonemitsu, O.. Eur. J. Org. Chem., 2001, 3615.
- 15a Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A.. J. Org. Chem., 1995, 60, 5048.
- 15b Ziegler, F. E.; Wallace, O. B.. J. Org. Chem., 1995, 60, 3626.
- 16 Zhao, X. Z.; Tu, Y. Q.; Peng, L.; Li, X. Q.; Jia, Y. X.. Tetrahedron Lett., 2004, 45, 3713.
