10.1002/adsc.201700879
Advanced Synthesis & Catalysis
[5] a) T. Mukaiyama, K. Banno, K. Narasaka, Chem.
Lett. 1973, 1011–1014; J. Am. Chem. Soc. 1974, 96,
7503–7509. b) T. Mukaiyama, Organic Reactions,
Wiley, New York, 1982; Vol. 28, pp 203.
water, brine, dried (Na2SO4) and concentrated. The
obtained crude product was purified by SiO2-column
chromatography (hexane-AcOEt = 10:1) to give the desired
product (10; 41 mg, 79%).
Pale yellow oil; 1H NMR (500 MHz,
[6] Self-type: a) Y. Tanabe, Bull. Chem. Soc. Jpn. 1989,
62, 1917–1924; b) Tanabe, Y.; Hamasaki, R.;
Funakoshi, S. Chem. Commun. 2001, 1674–1675;
c) Tanabe, Y.; Makita, A.; Funakoshi, S.;
Hamasaki, R.; Kawakusu, T. Adv. Synth. Catal.
2002, 344, 507–510.
acetone-6d) δ = 1.93 (d, J = 1.2 Hz,
3H), 3.67 (s, 3H), 3.90 (s, 3H), 6.20
(dq, J = 1.2, 10.3 Hz, 1H), 6.51 (d, J = 16.0 Hz, 1H), 6.72
(dd, J = 10.3, 16.0 Hz, 1H), 7.17–7.22 (m, 1H), 7.27–7.34
(m, 2H), 7.38–7.42 (m, 2H), 7.49 (s, 1H); 13C NMR (125
MHz, CDCl3) δ = 22.9, 51.3, 62.1, 111.0, 126.9 (2C), 127.9,
128.0, 129.4 (2C), 130.3, 131.2, 132.5, 138.8, 160.0, 167.6;
IR (neat): νmax = 1703, 1624, 1489, 1433, 1395, 1373, 1234,
1188; HRMS (ESI): m/z calcd for C16H18O3 [M + Na]+
281.1154; found: 281.1154. Physical properties of the
present synthetic strobilurin A exhibited in good agreement
with those derived from natural and synthetic specimens
(1H and 13C NMRs).[14c]
[7] Crossed-type: a) Ref. 6a; b) S. N. Crane, E. J.
Corey, Org. Lett. 2001, 3, 1395–1397; c) T. Misaki,
R. Nagase, K. Matsumoto, Y. Tanabe, J. Am. Chem.
Soc. 2005, 127, 2854–2855; d) A. Iida, S.
Nakazawa, T. Okabayashi, A. Horii, T. Misaki, Y.
Tanabe, Org. Lett. 2006, 8, 5215–5218; e) H.
Nakatsuji, H. Nishikado, K. Ueno, Y. Tanabe, Org.
Lett. 2009, 11, 4258–4261; f) Y. Ashida, S.
Kajimoto, H. Nakatsuji, Y. Tanabe, Org. Synth.
2016, 93, 286–305.
Acknowledgements
[8] Asymmetric version and its application to
asymmetric total synthesis of natural product: a) R.
Nagase, Y. Oguni, S. Ureshino, H. Mura, T. Misaki,
Y. Tanabe, Chem. Commun. 2013, 49, 7001–7003;
b) M. Sugi, R. Nagase, T. Misaki, H. Nakatsuji, Y.
Tanabe, Eur. J. Org. Chem. 2016, 4834–4841.
This research was partially supported by Grant-in-Aids for
Scientific Research on Basic Areas (B) “18350056”, Priority
Areas (A) “17035087” and “18037068”, (C) 15K05508, and
Exploratory Research “17655045” from the Ministry of
Education, Culture, Sports, Science and Technology (MEXT). We
thank Dr Ryohei Nagase and Mr Hiroshi Nishikado for their
assistances throughout the work.
[9] For selected examples, see: a) Y. Tanabe, N.
Matsumoto, T. Higashi, T. Misaki, T. Itoh, M.
Yamamoto, K. Mitarai, Y. Nishii, Tetrahedron
2002, 58, 8269–8280; b) Y. Tanabe, K. Mitarai, T.
Higashi, T. Misaki, Y. Nishii, Chem. Commun.
2002, 2542–2543; c) R. Nagase, N. Matsumoto, K.
Hosomi, T. Higashi, S. Funakoshi, T. Misaki, Y.
Tanabe, Org. Biomol. Chem. 2007, 5, 151–159.
One of the author (Y.T.) offers his warmest congratulations to
Professor Ben L. Feringa (University of Groningen, The
Netherlands) on being awarded the 2016 Nobel Prize in
Chemistry. Dedication to Professor Teruaki Mukaiyama on the
celebration of his 90th birthday (Sotuju)
References
[10] a) M. Periasamy, S. Suresh, and S. S. Ganesan,
Tetrahedron Lett. 2005, 46, 5521; b) S. Kikuchi, T.
Kobayashi, Y. Hashimoto, Tetrahedron Lett. 2006,
47, 1973; c) T. Funatomi, S. Nakazawa, K.
Matsumoto, R. Nagase, Y. Tanabe, Chem. Commun.
2008, 771–773.
[1] a) C. H. Heathcock, in: Comprehensive Organic
Synthesis, Vol 2, (Eds.: B. M. Trost, I. Fleming),
Pergamon: Oxford, 1991, pp 181; b) M. T. Smith,
March’s Advanced Organic Chemistry, Wiley, 6 th
ed., New York, 2007, pp 624, 1355, 1452; c) J.
Clayden, N. Greeves, S. Warren and P. Wothers,
Organic Chemistry, Oxford: New York, 2001, 689;
d) R. Mahrwald, Modern Aldol Reactions, Wiley-
VCH, Weinheim, 2004.
[11] J. M. Álvarez-Calero, Z. D. Jorge, G. M. Massanet,
Org. Lett. 2016, 18, 6344–6347.
[12] a) Y. Tanabe, N. Manta, N. R. Nagase, R. T.
Misaki, Y. Nishii, M. Sunagawa, A. Sasaki, Adv.
Synth. Catal. 2003, 345, 967–970; b) R. Nagase, H.
Gotoh, M. Katayama, N. Manta, Y. Tanabe,
Heterocycles 2007, 72, 697–708.
[2] a) E. J. Corey, R. Imwinkelreid, S. Pikul, Y. B.
Xiang, J. Am. Chem. Soc. 1989, 111, 5493–5495;
b) E. J. Corey, S. S. Kim, J. Am. Chem. Soc. 1990,
112, 4976–4977; c) E. J. Corey, D. -H. Lee,
Tetrahedron Lett. 1993, 34, 1737–1740.
[13] a) M. Sunagawa, H. Matsumura, T. Inoue, M.
Funasaka, M. Kato, J. Antibiot. 1990, 43, 519–532;
b) M. Sunagawa, A. Sasaki, Heterocycles 2001, 54,
497–528.
[3] a) H. C. Brown, K. Ganesan, Tetrahedron Lett.
1992, 33, 3421–3424; b) H. C. Brown, K. Ganesan,
J. Org. Chem. 2002, 67, 5250–5256.
[14] Review: a) J. M. Clough, Nat. Prod. Rep. 1993, 10,
565–574. Isolation and structure determination: b)
V. Musílek, F. Nerud, M. Vondráček, Folia
Microbiol. (Prague) 1969, 14, 377–378; c) G.
Schramm, W. Steglich, T. Anke, F. Oberwinkler,
Chem. Ber. 1978, 8, 2779–2784. d) T. Anke, G.
[4] a) A. Abiko; J.-F. Liu, S. Masamune, J. Org. Chem.
1996, 61, 2590–2591; b) A. Abiko, T. Inoue, S.
Masamune, J. Am. Chem. Soc. 2002, 124, 10759–
10764; c) A. Abiko, Acc. Chem. Res. 2004, 37,
387–395.
13
This article is protected by copyright. All rights reserved.