10.1002/chem.202100804
Chemistry - A European Journal
FULL PAPER
[13] a) T. Ogiku, S. Yoshida, M. Takahashi, T. Kuroda, H. Ohmizu, T.
Iwasaki, Tetrahedron Lett. 1992, 33, 4473-4476; b) Y. Kawabe, R.
Ishikawa, Y. Akao, A. Yoshida, M. Inai, T. Asakawa, Y. Hamashima, T.
Kan, Org. Lett. 2014, 16, 1976-1979.
Keywords: Borate • Hydroboration • Lignans • Suzuki-Miyaura
Coupling • Total Synthesis
[14] E. Alfonzo, A. B. Beeler, Chem. Sci. 2019, 10, 7746-7754.
[15] a) H. C. Brown, C. D. Pfaffenberger, J. Am. Chem. Soc. 1967, 89, 5475-
5477; b) H. C. Brown, E. Negishi, P. L. Burke, J. Am. Chem. Soc. 1972,
94, 3561-3567; c) H. C. Brown, E. Negishi, J. Am. Chem. Soc. 1972, 94,
3567-3572; d) P. L. Burke, E. Negishi, H. C. Brown, J. Am. Chem. Soc.
1973, 95, 3654-3662.
[1]
a) W. Adriani, Z. Untersuch. Lebensm. 1928, 56, 187-194; b) S. H.
Bertram, J. P. K. van der Steur, H. I. Waterman, Biochem. Z. 1928, 197,
1-7.
[2]
[3]
J. R. Cole, E. Bianchi, E. R. Trumbull, J. Pharm. Sci. 1969, 58, 175-176.
M. Chen, N. Kilgore, K.-H. Lee, D.-F. Chen, J. Nat. Prod. 2006, 69,
1697-1701.
[16] H. C. Brown, D. Basavaiah, N. G. Bhat, J. Org. Chem. 1986, 51, 4518-
4521.
[4]
[5]
a) J. L. Hartwell, A. W. Schrecker, J. Am. Chem. Soc. 1951, 73, 2909-
2916; b) A. W. Schrecker, J. L. Hartwell, J. Am. Chem. Soc. 1956, 21,
381-382.
[17] a) N. Miyaura, A. Suzuki, J. Chem. Soc., Chem. Commun. 1979, 866-
867; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
[18] a) G. Zweifel, H. C. Brown, J. Am. Chem. Soc. 1963, 85, 2066-2072; b)
E. Negishi, H. C. Brown, Synthesis 1974, 2, 77-89.
a) D. C. Ayres, J. D. Loike, Lignans: Chemical, biological, and clinical
properties, Cambridge University Press, London, 1990; b) F. G. Calvo-
Flores, J. A. Dobado, J. Isac-García, F. J. Martín-MartíNez, Lignin and
Lignans as Renewable Raw Materials: Chemistry, Technology and
Applications, Johm Wiley & Sons Ltd, West Sussex, 2015.
Oxidative dimerization of coniferyl alcohol, see: a) L. B. Davin, H.-B.
Wang, A. L. Crowell, D. L. Bedgar, D. M. Martin, S. Sarkanen, N. G.
Lewis, Science 1997, 275, 362-367; b) B. Pickel, M.-A. Constantin, J.
Pfannstiel, J. Conrad, U. Beifuss, A. Schaller, Angew. Chem. Int. Ed.
2010, 49, 202-204; Angew. Chem. 2010, 122, 207-209; c) B. Pickel, A.
Schaller, Appl. Microbiol. Biotechnol. 2013, 97, 8427-8438.
Review about biosynthesis of lignans and monolignols, see; a) R. A.
Dixon, M. S. S. Reddy, Phytochem. Rev. 2003, 2, 289-306; b) T.
Umezawa, Phytochem. Rev. 2003, 2, 371-390; c) S. Suzuki, T.
Umezawa, J. Wood Sci. 2007, 53, 273-284.
[19] R. Suzuki, S. Fuse, H. Tanaka, Eur. J. Org. Chem. 2016, 21, 3478-3481.
[20] K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461-470.
[21] K. Sato, Z. Omahdi, K. Shibata, K. Sonoda, S. Yamasaki, H. Tanaka,
Chem. Eur. J. 2017, 23, 16374-16379.
[6]
[22] For selected studies on diastereoselective cyclic hydroboration, see; a)
W. C. Still, K. P. Darst, J. Am. Chem. Soc. 1980, 102, 7385-7387; b) D.
J. Morgans Jr., Tetrahedron Lett. 1981, 22, 3721-3724; c) W. C. Still, K.
R. Shaw, Tetrahedron Lett. 1981, 22, 3725-3728; d) Y. Yokoyama, Y.
Terada, H. Kawashima, Chem. Lett. 1989, 18, 453-456; e) Y. Yokoyama,
Y. Terada, H. Kawashima, Bull. Chem. Soc. Jpn. 1991, 64, 2563-2565;
f) Y. Yokoyama, H. Kawashima, M. Kohno, Y. Ogawa, S. Uchida,
Tetrahedron Lett. 1991, 32, 1479-1482; g) G. Laschober, M. Zorzi, K.
J. Hodgetts, Molecules 2001, 6, 244-252; h) S. V. Pronin, M. G. Tabor,
D. J. Jansen, R. A. Shenvi, J. Am. Chem. Soc. 2012, 134, 2012-2015.
[23] See Supporting Information for details.
[7]
[8]
[9]
F. Zalesak, D. J.-Y. D. Bon, J. Pospisil, Pharmacol. Res. 2019, 146,
104284.
a) M. G. Kelly, J. L. Hartwell, J. Nat. Canc. Inst. 1954, 14, 967-1010; b)
T. O. Cockayne, Lecchdom, Wortcunnings and Starcraft of Early
England, vol II., The Holland Press, London, 1961.
[24] R. Damico, J. Org. Chem. 1964, 29, 1971-1976.
[25] B. Atasoy, R. Özen, Tetrahedron 1997, 53, 13867-13872
[26] a) T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett. 1980, 21, 1357-
1358; b) R. Noyori, S. Murata, M. Suzuki, Tetrahedron 1981, 37, 3899-
3910.
[10] For selected recent reviews of synthesis of lignan, see; a) J.-Y. Pan, S.-
L. Chen, M.-H. Yang, J. Wu, J. Sinkkonen, K. Zou, Nat. Prod. Rep. 2009,
26, 1251-1292; b) G. E. Magoulas, D. Papaioannou, Molecules 2014,
19, 19769-19835; c) X. Fang, X. Hu, X., Molecules 2018, 23, 3385.
[11] For selected recent synthetic studies of lignans, see; a) J. Xiao, X.-W.
Cong, G.-Z. Yang, Y.-W. Wang, Y. Peng, Org. Lett. 2018, 20, 1651-
1654; b) G. Liao, Q.-J. Yao, Z.-Z. Zhang, Y.-J. Wu, D.-Y. Huang, B.-F.
Shi, Angew. Chem. Int. Ed. 2018, 57, 3661-3665; Angew. Chem. 2018,
130, 3723-3727; c) P. Hartmann, M. Lazzarotto, L. Steiner, E. Cigan, S.
Poschenrieder, P. Sagmeister, M. Fuchs, J. Org. Chem. 2019, 84,
5831-5837; d) C. P. Ting, E. Tschanen, E. Jang, T. J. Maimone,
Tetrahedron 2019, 75, 3299-3308; e) J. Li, X. Zhang, H. Renata, Angew.
Chem. Int. Ed. 2019, 58, 11657-11660; Angew. Chem. 2019, 131,
11783-11786; g) M. Kobayashi, H. Ueno, N. Yoshida, H. Ouchi, T.
Asakawa, F. Yoshimura, M. Inai, T. Kan, J. Org. Chem. 2019, 84,
14227-14240.
[27] a) H. C. Brown, E. Negishi, J.-J. Katz, J. Am. Chem. Soc. 1972, 94,
5893-5894; b) H. C. Brown, E. Negishi, J.-J. Katz, J. Am. Chem. Soc.
1975, 97, 2791-2798.
[28] Brown had claimed that cyclic hydroboration of exo-cylcic diene should
be potent to afford both of cis- and trans-bicyclic boranes, see: H. C.
Brown, E. Negishi, Tetrahedron 1977, 33, 2331-2357.
[29] H. C. Brown, G. W. Kramaer, J. L. Hubbar, S. Krishnamurthy, J.
Organomet. Chem. 1980, 188, 1-10.
[30] In order to suppress the reduction, we first investigated the use of
additives (TMEDA, DMPU, or HMPA) to enhance the nucleophilicity of
organolithium reagents, but these attempts failed.
[31] N. Rehnberg, G. Magnusson, J. Org. Chem. 1990, 55, 4340-4349.
[32] a) F. Rogano, G. Froidevaux, P. Ruedi, Helv. Chim. Acta 2010, 93,
1299-1312; b) N. Shiraishi, M. Kumazoe, S. Fuse, H. Tachibana, H.
Tanaka, Chem. Eur. J. 2016, 22, 13050-13053.
[12] a) F. Chioccara, S. Poli, B. Rindone, T. Pilati, G. Brunow, P. Pietikainen,
H. Setala, Acta Chem. Scand. 1993, 47, 610-616; b) D. Fournand, B.
Cathala, C. Lapierre, Phytochemistry 2003, 62, 139-146; c) F. Saliu, E.-
L. Tolppan, L. Zoia, M. Orlandi, Tetrahedron Lett. 2011, 52, 3856-3860;
d) E. C. Aka, E. Wimmer, E. barre, N. Vasudevan, D. Cortes-Borda, T.
Ekou, L. Ekou, M. Rodriguez-Zubiri, F.-X. Felpin, J. Org. Chem. 2019,
84, 14101-14112.
[33] H. Yamada, K. Nagao, D. Dokei, Y. Kasai, N. Michihara, J. Am. Chem.
Soc. 2008, 130, 7566-7567.
[34] W. S. Woo, K. H. Shin, H. Wagner, H. Lotter, Phytochemistry 1987,
26, 1542-1543.
7
This article is protected by copyright. All rights reserved.