Ya-mu XIA, Wei WANG, Ying-lan Guo And Jun-feng LI, Ying-lan GUO, Jun-feng LI

Asymmetric synthesis of 8-O-4'-neolignan perseal B

Full details of an enantioselective total synthesis of 8-O-4'-neolignan perseal B are presented for the first time. The synthesis was achieved in 8 steps from vanillin and involved the asymmetric dihydroxylation reaction using AD-mix-a to give the key intermedium (1S,2S)-1-(4-(benzyloxy)-3-methoxyphenyl)propane-1,2,3- triol, and the Mitsunobu reaction between phenylpropanoid and vanillin formed perseal B. The synthetic method of perseal B exhibits a new route for 8-O-4'-neolignan.

Anahtar Kelimeler:

Neolignans; perseal B; enantioselective synthesis.

Asymmetric synthesis of 8-O-4'-neolignan perseal B

Keywords:

Neolignans; perseal B; enantioselective synthesis.,

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Ward, R. S. Nat. Prod. Rep. 1999, 16, 75-96.
Chen, X. C.; Ren, X. F.; Peng, K.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron: Asymmetr 2003, 14, 704.
Tsai, I. L.; Hsieh, C. F.; Duh, C. Y.; Chen, I. S. Phytochemistry. 1996, 43, 1261-1263.
Hanessian, S.; Reddy, G. J.; Chahal, N. Org. Lett. 2006, 8, 5477-5480.
Nocito, I.; Castelli, M. V.; Zacchino, S. A.; Serra, E. Parasitol Res. 2007, 101, 1453-1457.
Gottlieb, O. R.; Yoshida, M. Quim. Nova. 1984, 7, 250-273.
Lourith, N.; Katayama,T.; Suzuki, T. J. Wood. Sci. 2005, 51, 370-378.
Iyer, M. R.; Baskaran, S.; Trivedi, G. K. J. Indian Chem. Soc. 1994, 71, 341-343.
Zanarotti, A. J. Chem. Research (S). 1983, 306-307.
Braga, A. C. H.; Zacchino, S.; Badano, H.; Sierra, M. G.; Ruveda, E. A. Phytochemistry. 1984, 23, 2025-2028.
Curti, C.; Zanardi, F.; Battistini, L.; Sartori, A.; Rassu, G.; Pinna, L.; Casiraghi, G. J. Org. Chem. 2006, 71, 8558.
Gu, W. X.; Chen, X. C.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron: Asymmetr 2000, 11, 2801-2807.
Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D. Q.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768-2771.
Mitsunobu. O. Synthesis, 1981, 1-26.