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Synlett

Volumn , Issue 2, 2009, Pages 292-296

Cyclohepta[de]naphthalenes and the rearranged abietane framework of microstegiol via Nicholas reaction chemistry

(3) Taj, Rafiq A a Abhayawardhana, Anusha a Green, James R a

a UNIVERSITY OF WINDSOR (Canada)

Author keywords

Alkyne complexes; Carbocations; Electrophilic aromatic substitution; Ring closure; Tautomerism; Transition metals

Indexed keywords

EID: 62349128135 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087521 Document Type: Article

Times cited : (8)

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34
- 62349121178
- 4Cl was added, and the mixture subjected to a conventional extractive workup. Purification by flash chromatography afforded 3 (monocondensation) or 4 and 5 (dicondensation).
- 4Cl was added, and the mixture subjected to a conventional extractive workup. Purification by flash chromatography afforded 3 (monocondensation) or 4 and 5 (dicondensation).

35
- 62349091338
- Analytical Data for Selected Compounds Compound 3a: IR (KBr, νmax, 3003, 2960, 2090, 2055 cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.71 (d, J, 8.9 Hz, 1 H, 7.70 (d, J, 8.9 Hz, 1 H, 7.22 (d, J, 2.4 Hz, 1 H, 7.10 (d, J, 8.9 Hz, 1 H, 7.04 (dd, J, 8.9, 2.4 Hz, 1 H, 5.95 (s, 1 H, 4.60 (s, 2 H, 3.97 (s, 3 H, 3.94 (s, 3 H, 13C NMR (125 MHz, CDCl3, δ, 199.6, 158.4, 154.7, 133.9, 130.2, 128.6, 124.6, 120.1, 116.1, 109.7, 101.6, 96.1, 73.5, 55.4, 55.1, 29.5. MS: m/e, 484 [M, CO, 456 [M, 2 CO, 428 [M, 3 CO, 372 [M, 5 CO, HRMS: m/e calcd for C21H 14Co2O8 [M, 2 CO, 455.9454; found: 455.9441. Compound 3b: IR (KBr, νmax, 3003, 2951, 2097, 2063, 2028, 1708 cm-1. 1H NMR 500 MHz, CDCl
- + - CO]: 541.9458; found: 541.9455.

36
- 62349128581
- However, substitution at the propargylic site in 2 resulted in condensation reactions at C-3 in preference to C-1.
- However, substitution at the propargylic site in 2 resulted in condensation reactions at C-3 in preference to C-1.

37
- 62349102966
- Analytical Data for Selected Compounds Compound 4a: IR (KBr, νmax, 2917, 2090, 2051, 2021 cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.70 (d, J, 8.9 Hz, 2 H, 7.12 (d, J, 8.9 Hz, 2 H, 5.83 (s, 2 H, 5.22 (d, J, 16.4 Hz, 2 H, 4.50 (d, J, 16.4 Hz, 2 H, 3.99 (s, 6 H, 13C NMR (125 MHz, CDCl3, δ, 199.6, 156.1, 131.9, 130.7, 126.5, 121.3, 110.1, 97.5, 73.8, 55.9, 30.6. MS: m/e, 808 [M, 1 CO, 780 [M, 2 CO, 752 [M, 3 CO, 724 [M, 4 CO, 696 [M, 5 CO, 668 [M, 6 CO, 640 [M, 7 CO, 612 [M, 8 CO, HRMS: m/e calcd for C30H16Co4O14 [M, CO, 807.7917; found: 807.7904. Compound 4b: IR (KBr, νmax, 3004, 2950, 2097, 2067, 1710 cm-1. 1H NMR 500 MHz, CDCl
- + - 9 CO].

38
- 62349095231
- Compound 6: IR (KBr, νmax, 3291, 2932, 2107, 1618 cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.72 (d, J, 9.0 Hz, 2 H, 7.18 (d, J, 9.0 Hz, 2 H, 4.31 (d, J, 2.6 Hz, 4 H, 4.03 (s, 6 H, 2.16 (t, J, 2.6 Hz, 2 H, 13C NMR (125 MHz, CDCl3, δ, 156.7, 133.5, 130.1, 126.2, 117.3, 111.0, 84.7, 69.1, 56.9, 17.3. MS: m/e, 264 [M, HRMS: m/e calcd for C18H16O2 [M, 264.1150; found: 264.1153. Compound 7: IR (KBr, νmax, 3077, 2934, 1614 cm-1. 1H NMR (300 MHz, CDCl 3, δ, 7.72 (d, J, 8.9 Hz, 2 H, 7.18 (d, J, 8.9 Hz, 2 H, 6.23 (m, 2 H, 5.09 (dd J, 10.3, 1.9 Hz, 2 H, 4.84 (dd, J, 17.3, 1.9 Hz, 2 H, 3.93 (s, 6 H, 3.91 (m, 4 H, 13C NMR 75 MHz, CDCl3, δ, 156.7, 139.0, 134.9
- +]: 240.1150; found: 240.1150.

39
- 33750552076
- (a) Kotha, S.; Mandal, K.; Tiwari, A.; Mobin, S. M. Chem. Eur. J. 2006, 12, 8024.
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- Kotha, S.¹ Mandal, K.² Tiwari, A.³ Mobin, S.M.⁴

40
- 34248589185
- (b) Chattopadhyay, S. K.; Ghosh, D.; Neogi, K. Synth. Commun. 2007, 37, 1535.
- (2007) Synth. Commun , vol.37 , pp. 1535
- Chattopadhyay, S.K.¹ Ghosh, D.² Neogi, K.³

41
- 62349108620
- Analytical Data for Selected Compounds Compound 10: IR (KBr, νmax, 2956, 2233, 1712, 1628 cm-1. 1H NMR (500 MHz, CDCl3, δ, 7.72 (d, J, 9.0 Hz, 1 H, 7.69 (d, J, 8.9 Hz, 1 H, 7.22 (d, J, 2.4 Hz, 1 H, 7.11 (d, J, 9.0 Hz, 1 H, 7.05 (dd, J, 8.9, 2.4 Hz, 1 H, 4.11 (s, 2 H, 3.97 (s, 3 H, 3.96 (s, 3 H, 3.70 (s, 3 H, 13C NMR (125 MHz, CDCl3, δ, 158.4, 154.6, 154.0, 133.7, 129.9, 128.9, 124.3, 116.1, 113.6, 110.1, 101.2, 87.7, 71.9, 56.1, 55.0, 52.2, 14.5. MS: m/e, 284 [M, HRMS: m/e calcd for C 17H16O4 [M, 284.1049; found: 284.1033. Compound 11: IR (KBr, νmax, 2954, 1740, 1628 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.69 (d, J, 8.9 Hz, 1 H, 7.66 (d, J, 8.9 Hz, 1 H, 7.32 d, J, 2.0 Hz, 1
- +]: 270.1620; found: 270.1614.

42
- 62249223982
- Analytical Data for Selected Compounds Compound 17: IR (KBr, νmax, 3004, 2952, 2099, 2063, 2029,1765, 1709 cm -1. 1H NMR (500 MHz, CDCl3, δ, 7.82 (d, J, 9.0 Hz, 1 H, 7.81 (d, J, 8.8 Hz, 1 H) 7.61 (d, J, 2.2 Hz, 1 H, 7.26 (d, J, 9.0 Hz, 1 H, 7.11 (dd, J, 8.8, 2.2 Hz, 1 H, 4.60 (s, 2 H, 3.96 (s, 3 H, 3.75 (s, 3 H, 2.33 (s, 3 H, 13C NMR (125 MHz, CDCl3, δ, 198.0, 170.5, 169.4, 154.7, 149.3, 133.2, 130.0, 128.8, 126.8, 120.0, 118.6, 114.1, 111.8, 98.5, 93.9, 55.2, 52.5, 28.2, 20.8. MS: m/e, 542 [M, 2 CO, 514 [M, 3 CO, 486 [M, 4 CO, 458 [M, 5 CO, 430 [M, 6 CO, HRMS: m/e calcd for C24H 16Co2O11 [M, 3 CO, 513.9509; found: 513.9511. Compound 18: IR KBr, νmax, 2917, 2234, 1761
- +]: 242.0943; found: 242.0931.

43
- 78650267327
- (a) Rieche, A.; Fruhwald, E. Ber. Dtsch. Chem. Ges. B 1931, 64, 1603.
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- Rieche, A.¹ Fruhwald, E.²

44
- 33846697730
- (b) Moghaddam, F. M.; Porkaleh, H.; Zali-Boeini, H. Lett. Org. Chem. 2006, 3, 123.
- (2006) Lett. Org. Chem , vol.3 , pp. 123
- Moghaddam, F.M.¹ Porkaleh, H.² Zali-Boeini, H.³

45
- 62349124340
- Analytical Data for Selected Compounds Compound 21: IR (KBr, νmax, 3358, 2967 cm-1. 1H NMR (500 MHz, CDCl3, δ, 8.10 (br s, 1 H, 7.65 (d, J, 8.8 Hz, 1 H, 7.61 (d, J, 8.9 Hz, 1 H, 7.33 (d, J, 2.2 Hz, 1 H, 7.08 (d, J, 8.9 Hz, 1 H, 7.01 (dd, J, 8.8, 2.2 Hz, 1 H, 3.91 (s, 3 H, 2.95 (br t, J, 7.0 Hz, 2 H, 2.60 (br s, 1 H, 1.65 (m, 4 H, 1.21 (s, 6 H, 13C NMR (125 MHz, CDCl3, δ, 154.6, 154.5, 134.4, 130.3, 127.3, 124.5, 122.1, 115.6, 110.7, 105.3, 72.0, 56.4, 43.5, 29.1, 25.4, 24.3. MS: m/e, 274 [M, HRMS: m/e calcd for C17H22O3: 274.1569; found: 274.1574. Compound 22: IR (KBr, νmax, 2934, 1653, 1615 cm -1. 1H NMR (500 MHz, CDCl3, δ, 7.29 (d, J, 9.7 Hz, 1 H, 7.13 (d, J, 8.4 Hz, 1 H, 6.79 d, J
- 2: 256.1463; found: 256.1457.

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