K. Kumar, S. S. More, G. L. Khatik, R. K. Rawal, and V. A. Nair
Vol 000
130.2, 123.6, 117.8, 106.0, 104.9, 87.9, 67.4, 41.1, 31.2;
ESI-HRMS (m/z): [M + H]+ calcd. For C11H14NO2,
192.1025, found 192.1024.
127.3, 127.1, 124.4, 106.3, 103.9, 103.4, 88.1, 67.3, 49.4,
41.3, 20.7; ESI-HRMS (m/z): [M + Na]+ calcd. For
C18H19NNaO2, 304.1313, found 304.1310.
8-Benzyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indol-3a-ol
(10b). Pink solid, m.p. = 104-106°C; [a]2D2 = (+)52.5 (c
1
REFERENCES AND NOTE
1.00, CHCl3); H NMR (CDCl3, 400 MHz) δ 7.35–7.32
(m, 5H), 7.29–7.26 (m, 1H), 7.18–7.14 (m, 1H), 6.76 (t,
J = 7.4 Hz, 1H), 6.40 (d, J = 7.9 Hz, 1H), 5.33 (s, 1H),
4.51 (q, J = 16.0 Hz, 2H), 4.13–4.08 (m, 1H), 3.73–3.67
(m, 1H), 2.50–2.45 (m, 1H), 2.40–2.36 (m, 1H), 2.29 (brs,
1H); 13C NMR (CDCl3, 100 MHz) δ 150.4, 138.2, 130.4,
130.2, 128.6, 127.4, 127.2, 123.8, 118.0, 106.4, 103.6,
88.0, 67.3, 49.1, 41.4; ESI-HRMS (m/z): [M + Na]+ calcd.
For C17H17NNaO2, 290.1157, found 290.1153.
[1] (a) Koehn, F. E.; Carter, G. T. Nat Rev Drug Discov 2005, 4,
206; (b) Berlinck, R. G. S. J Nat Prod 2012, 75, 1256; (c) Dias, D. A.;
Urban, S.; Roessner, U. Metabolites 2012, 2, 303 and reference cited therein.
[2] (a) Kan, S. B. J.; Ng, K. K.-H.; Paterson, I. Angew Chem
Inter Ed 2013, 52, 9097; (b) Kalesse, M.; Cordes, M.; Symkenberg, G.;
Lu, H.-H. Nat Prod Rep 2014, 31, 563 and reference cited therein.
[3] (a) Robinson, B. In The AlkaloidsManske, R. H. F. Ed.; Aca-
demic Press: New York, 1968; Vol X Chapter 5; (b) The Alkaloids;
Manske, R. H. F. Vol; Academic Press: New York, 1971 XIII, Chapter
4; (c) Yu, Q.; Liu, C.; Brzostowska, M.; Chrisey, L.; Brossi, A.; Greig,
N. H.; Atack, J. R.; Soncrant, T. T.; Rapoport, S. I.; Radunz, H. Helv
Chim Acta 1991, 74, 761; (d) Brzostowska, M.; He, X.; Greig, N. H.;
Stanley, S. I.; Brossi, A. Med Chem Res 1992, 2, 238; (e) Kawashima,
A.; Seto, H.; Kato, M.; Yasuda, A.; Uchida, K.; Otake, N. J Antibiot
1986, 39, 1495.
5-Bromo-8-methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]
indol-3a-ol (10c).
Yellow liquid; [a]2D2 = (+)62.7 (c
1
1.00, CHCl3); H NMR (CDCl3, 400 MHz) δ 7.28 (d,
J = 2.2 Hz, 1H), 7.20–7.18 (m, 1H), 6.38 (d, J = 8.4 Hz,
1H), 5.23 (s, 1H), 4.13–4.10 (m, 1H), 3.65–3.64 (m, 1H),
2.94 (s, 3H), 2.48–2.44 (m, 1H), 2.36–2.35 (m, 1H); 13C
NMR (CDCl3, 100 MHz) δ 149.8, 133.0, 132.3, 126.7,
109.0, 107.4, 104.9, 87.6, 67.4, 41.2, 30.2; ESI-HRMS
(m/z): [M + Na]+ calcd. For C11H12BrNNaO2, 291.9949,
found 290.9837.
[4] Takano, S.; Ogasawara, K. In The AlkaloidsBrossi, A. Ed.;
Academic: New York, 1989; Vol 36, p. 225.
[5] (a) Greig, N. H.; Pei, X.-F.; Soncrant, T. T.; Ingram, D. K.;
Brossi, A. Med Res Rev 1995, 15, 3; (b) Sano, N.; Bell, K.; Marder, K.;
Stricks, L.; Stern, Y.; Mayeux, R. Clin Neuropharmacol 1993, 16, 61.
[6] Hayashi, M.; Kim, Y.-P.; Takamatsu, S.; Enomoto, A.;
Shinose, M.; Takahashi, Y.; Tanaka, H.; Komiyama, K.; Omura, S. J
Antibiot 1996, 49, 1091.
[7] Takamatsu, S.; Kim, Y.-P.; Enomoto, A.; Hayashi, M.;
Tanaka, H.; Komiyama, K.; Omura, S. J Antibiot 1997, 50, 1069.
[8] Kawagishi, H.; Hota, K.; Masuda, K.; Yamaguchi, K.;
Yazawa, K.; Shibata, K.; Uzuka, N.; Matahira, Y. Biosci Biotechnol
Biochem 2006, 70, 2800.
[9] (a) Yu, Q. S.; Lu, B. Y. Heterocycles 1994, 39, 519; (b) Yu,
Q.; Liu, C.; Brzostowska, M.; Chrisev, L.; Brossi, A.; Greig, N. H.; Atack,
J. R.; Soncrant, T. T.; Rapoport, S. I.; Radunz, H. Helv Chim Acta 1991,
74, 761; (c) Luo, Y.; Yu, Q.; Chrisey, L.; Brossi, A. Heterocycles 1990,
31, 283.
[10] Morales-Ríos, M. S.; Santos-Sánchez, N. F.; Joseph-Nathan,
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31, 219.
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T.; Handa, M.; Yamamoto, D.; Harigaya, Y.; Kuwajima, I.; Omura, S.
Tetrahedron Lett 2005, 46, 1459.
8-Benzyl-5-bromo-3,3a,8,8a–tetrahydro-2H-furo[2,3-b]
indol-3a-ol (10d). Brownish liquid; [a]2D2 = (+)54.8 (c
1.00, CHCl3); H NMR (CDCl3, 400 MHz) δ 7.35–7.32
1
(m, 5H), 7.16 (t, J = 7.9 Hz, 1H), 6.76 (t, J = 7.4 Hz, 1H),
6.40 (d, J = 7.9 Hz, 1H), 5.35 (s, 1H), 4.52 (q,
J = 16.0 Hz, 2H), 4.15–4.10 (m, 1H), 3.74–3.68 (m, 1H),
2.54–2.46 (m, 1H), 2.41–2.31 (m, 2H); 13C NMR (CDCl3,
100 MHz) δ 150.4, 138.1, 130.4, 130.1, 128.6, 127.4,
127.2, 123.8, 118.0, 106.4, 103.6, 88.1, 67.3, 49.1, 41.4;
ESI-HRMS (m/z): [M + Na]+ calcd. For C17H16BrNNaO2,
369.2082, found 369.1788.
5,8-Dimethyl-3,3a,8,8a–tetrahydro-2H-furo[2,3-b]indol-3a-
ol (10e).
Yellowish liquid; [a]2D2 = (+)59.2 (c 1.00,
1
CHCl3); H NMR (CDCl3, 400 MHz) δ 7.12 (s, 1H),
6.81–6.79 (m, 1H), 6.36 (d, J = 8.0 Hz, 1H), 5.18 (s,
1H), 4.09–4.06 (m, 1H), 3.90–3.85 (m, 1H), 3.64–3.58
(m, 1H), 3.25 (s, 3H), 3.03–3.00 (m, 1H), 2.91 (s, 3H);
13C NMR (CDCl3, 100 MHz) δ 148.9, 138.7, 130.8,
125.7, 109.7, 106.0, 105.4, 88.0, 67.4, 41.0, 31.7, 20.7;
ESI-HRMS (m/z): [M + H]+ calcd. For C12H16NO2,
206.1181, found 206.1174.
[13] (a) Tanaka, K.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett
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Pharm Bull 1996, 44, 715.
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Tetrahedron 2000, 56, 1469; (b) Clark, A. J.; Jones, K. Tetrahedron
1992, 48, 6875.
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2, 2757; (b) Morales-Rios, M. S.; Santos-Sanchez, N. F.; Fragoso-
Vazquez, M. J.; Alagille, D.; Villagomez-Ibarra, J. R.; Joseph-Nathan, P.
Tetrahedron 2003, 59, 2843; (c) Tadamasa, O. Tetrahedron Lett 1971,
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M.; Komiyama, K.; Omura, S.; Smith, A. B. J Am Chem Soc 2000, 122,
8-Benzyl-5-methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]
indol-3a-ol (10f).
Pink solid, m.p. = 100–102°C; [a]
22
= (+)45.4 (c 1.00, CHCl3); 1H NMR (CDCl3,
D
400 MHz) δ 7.36–7.31 (m, 4H), 7.27–7.25 (m, 1H), 7.14
(s, 1H), 6.96 (dd, J = 1.0, 7.0 Hz, 1H), 6.31 (d,
J = 8.0 Hz, 1H), 5.33 (s, 1H), 4.49 (q, J = 16.0 Hz, 2H),
4.13–4.09 (m, 1H), 3.74–3.68 (m, 1H), 2.52–2.44 (m, 1H),
2.40–2.35 (m, 1H), 2.29 (s, 3H), 2.12 (brs, 1H); 13C NMR
(CDCl3, 100 MHz) δ 148.3, 138.3, 130.8, 130.2, 128.5,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet