Synlett 2011(16): 2397-2401  
DOI: 10.1055/s-0030-1261221
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Vinylogous Nicholas Reactions in the Synthesis of Icetexane, Faveline, and Related Ring Systems

Izabela Kolodziej, James R. Green*
Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada
Fax: +1(519)9737098; e-Mail: jgreen@uwindsor.ca;
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Publikationsverlauf

Received 11 July 2011
Publikationsdatum:
08. September 2011 (online)

Abstract

The intramolecular vinylogous Nicholas reactions of aryl substituted acetoxy enyne-Co2(CO)6 complexes afford tricyclic 6,7,6-ring systems and related systems in good yield.

    References and Notes

  • 1 For a review, see: Green JR. Eur. J. Org. Chem.  2008,  6053 
  • 2a Green JR. Synlett  2001,  353 
  • 2b Young DGJ. Burlison JA. Peters U. J. Org. Chem.  2003,  68:  3494 
  • 3 Iwasawa N. Satoh H. J. Am. Chem. Soc.  1999,  121:  7951 
  • 4a Iwasawa N. Sakurada F. Iwamoto M. Org. Lett.  2000,  2:  871 
  • 4b Iwasawa N. Inaba K. Nakayama S. Aoki M. Angew. Chem. Int. Ed.  2005,  44:  7447 
  • 5a Tanino K. Kondo F. Shimizu T. Miyashita M. Org. Lett.  2002,  4:  2217 
  • 5b Tanino K. Simizu T. Miyama M. Kuwajima I. J. Am. Chem. Soc.  2000,  122:  6116 
  • 6 Inaba K. Tanaka J. Iwasawa N. Chem. Lett.  2007,  36:  474 
  • For recent reviews, see:
  • 7a Shea KM. In Name Reactions for Homologations   Part 1:  Li JJ. Wiley; Hoboken: 2009.  p.284-298  
  • 7b Diaz DD. Betancort JM. Martín VS. Synlett  2007,  343 
  • 7c Teobald BJ. Tetrahedron  2002,  58:  4133 
  • 7d Green JR. Curr. Org. Chem.  2001,  5:  809 
  • For extensive work on the cyclic ether analogues, see:
  • 8a Hamajima A. Isobe M. Angew. Chem. Int. Ed.  2009,  48:  2941 ; and references cited therein
  • 8b Baba T. Huang G. Isobe M. Tetrahedron  2003,  59:  6851 ; and references cited therein
  • 8c Isobe M. Nishizawa R. Hosokawa S. Nishikawa T. Chem. Commun.  1998,  2665 
  • 8d For a distinct approach to oxepanes involving a vinylogous Nicholas step, see: Gómez AM. Lobo F. Pérez de las Vacas D. Valverde S. López JC. Chem. Commun.  2010,  46:  6159 
  • 8e For a rare example of a cyclic amide analogue, see: Closser CD. Quintal MM. Shea KM. J. Org. Chem.  2009,  74:  3680 
  • 9a Ding Y. Green JR. Synlett  2005,  271 
  • 9b Djurdjevic S. Yang F. Green JR. J. Org. Chem.  2010,  75:  8241 
  • 10a Padmanabhan S. Nicholas KM. Tetrahedron Lett.  1982,  23:  2555 
  • 10b Shibuya S. Isobe M. Tetrahedron  1998,  54:  6667 
  • 10c Álvaro E. de la Torre MC. Sierra MA. Org. Lett.  2003,  5:  2381 
  • 10d DiMartino J. Green JR. Tetrahedron  2006,  62:  1402 ; and references cited therein
  • 11a Simmons EM. Sarpong R. Nat. Prod. Rep.  2009,  26:  1195 
  • 11b Endo Y. Ohta T. Nozoe S. Tetrahedron Lett.  1991,  32:  3083 
  • 12a Carita A. Burtoloso ACB. Tetrahedron Lett.  2010,  51:  686 
  • 12b Muratake H. Natsume M. Nakai H. Tetrahedron  2004,  60:  11783 
  • 12c Isobe S.-I. Kubo K. Thiemann T. Sawada T. Yonemitsu T. Mataka S. Bull. Chem. Soc. Jpn.  2002,  75:  773 
  • 12d Ho T.-L. Chen C.-K. Tetrahedron  1995,  51:  5819 
  • 12e Ghosh AK. Mukopadhyay C. Ghatak UR. J. Chem. Soc., Perkin Trans. 1  1994,  327 
  • 13a Majetich G. Zou G. Grove J. Org. Lett.  2008,  10:  85 
  • 13b Majetich G. Hicks R. Zhang Y. Tian X. Feltman TL. Fang J. Duncan S. J. Org. Chem.  1996,  61:  8169 
  • 13c Matsumoto T. Imai S. Yoshinari T. Matsuno S. Bull. Chem. Soc. Jpn.  1986,  59:  3103 
  • 14a Liu L. Gao Y. Che C. Wu N. Wang DZ. Li C.-C. Yang Z. Chem. Commun.  2009,  662 
  • 14b Tucket MW. Watkins WJ. Whitby RJ. Tetrahedron Lett.  1998,  39:  123 
  • 14c Sarkar A. Saha G. Ghosh S. J. Org. Chem.  1992,  57:  5771 
  • 14d Padwa A. Chughtai MJ. Tetrahedron  2008,  64:  4758 
  • 14e Padwa A. Boosombat J. Rashatasakhon P. Willis J. Org. Lett.  2005,  7:  3725 
  • 14f Oh CH. Lee SM. Hong CS. Org. Lett.  2010,  12:  1308 ; and references cited therein
  • 14g Sammes PG. Whitby RJ. J. Chem. Soc., Perkin Trans. 1  1987,  195 
  • 15a Saadi J. Reissig H.-U. Synlett  2009,  2089 
  • 15b Schneider G. Tapolcsányi P. Wölfling J. Müller P. Noltemeyer M. Terlau V. Synlett  2003,  1494 
  • 15c Ghosh AK. Mukhopadhyaya JK. Ghatak UR. J. Chem. Soc., Perkin Trans. 1  1997,  2747 
  • 15d Grant SW. Zhu K. Zhang Y. Castle SL. Org. Lett.  2006,  8:  1867 
  • 16a Sengupta S. Drew MGB. Mukhopadhyay R. Achari B. Banerjee AK. J. Org. Chem.  2005,  70:  7694 
  • 16b Maratake H. Natsune M. Nakai H. Tetrahedron  2004,  60:  11783 
  • 17a Payne AD. Skelton BW. Wege D. White AH. Eur. J. Org. Chem.  2007,  1184 
  • 17b Hauser FM. Yin H. Org. Lett.  2000,  2:  1045 
  • 18 Wang X. Pan X. Cui Y. Chen Y. Tetrahedron  1996,  52:  10659 
  • 19a Simmons EM. Hardin AR. Guo X. Sarpong R. Angew. Chem. Int. Ed.  2008,  47:  6650 
  • 19b Simmons EM. Sarpong R. Org. Lett.  2006,  8:  2883 
  • 19c Kurti L. Czako B. Corey EJ. Org. Lett.  2008,  10:  5247 
  • 19d Ranu BC. Jana U. J. Org. Chem.  1999,  64:  6380 
  • 20 These compounds were prepared from the corresponding iodoarenes, by known Sonogashira reactions with trimethylsilylacetylene followed by desilylation. See, for example: Montalbetti C. Savignac M. Bonnefis F. Genet JP. Tetrahedron Lett.  1995,  36:  5891 
  • 24a Kira K. Tanda H. Hamajima A. Baba T. Takai S. Isobe M. Tetrahedron  2002,  58:  6485 
  • 24b For related examples, see: Hosokawa S. Isobe M. Tetrahedron Lett.  1998,  39:  2609 
  • 24c Takai S. Ploypradith P. Hamajima A. Kira K. Isobe M. Synlett  2002,  588 
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Analytical Data for Selected Compounds
Compound 4g: IR (KBr): νmax = 2954, 2833, 2187, 1673 cm. ¹H NMR (500 MHz, CDCl3): δ = 10.35 (s, 1 H), 6.96 (d, J = 3.1 Hz, 1 H), 6.90 (dd, J = 9.1, 3.1 Hz, 1 H), 6.83 (d, J = 9.1 Hz, 1 H), 3.86 (s, 3 H), 3.79 (s, 3 H), 2.73 (m, 2 H), 2.55 (m, 2 H), 1.83 (m, 2 H), 1.70 (m, 1 H), 1.48 (m, 1 H). ¹³C NMR (75 MHz, CDCl3): δ = 193.0, 154.9, 153.2, 148.2, 145.9, 117.5, 116.8, 112.0, 111.9, 96.7, 91.9, 56.4, 55.8, 37.4, 32.3, 25.7, 24.2. MS: m/e = 284 [M+]. HRMS: m/e calcd for C18H20O3 [M+] 284.1412; found: 284.1412. Compound 5g: IR (KBr): νmax = 2964, 1746 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.93 (d, J = 2.9 Hz, 1 H), 6.81 (d of 0.5 ABquart, J = 2.9, 8.9 Hz, 1 H), 6.78 (0.5 ABquart, J = 8.9 Hz, 1 H), 4.97 (s, 2 H), 3.84 (s, 3 H), 3.77 (s, 3 H), 2.51 (m, 2 H), 2.32 (m, 2 H), 2.09 (s, 3 H), 1.79 (m, 2 H), 1.62 (m, 2 H), 1.53 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 171.2, 154.4, 153.1, 145.1, 126.0, 117.4, 115.4, 113.3, 111.9, 94.9, 89.9, 68.0, 56.4, 55.8, 34.6, 32.3, 31.2, 26.1, 26.0, 21.0. MS: m/e = 328 [M+]. HRMS: m/e calcd for C20H24O4 [M+]: 328.1675; found: 328.1683.
Compound 1g: IR (KBr): νmax = 2926, 2085, 2058, 2013, 1741 cm. ¹H NMR (500 MHz, CDCl3): δ = 7.01 (d, J = 3.1 Hz, 1 H), 6.86 (dd, J = 8.9, 3.1 Hz, 1 H), 6.75 (d, J = 8.9 Hz, 1 H), 4.53 (s, 2 H), 3.81 (s, 3 H), 3.75 (s, 3 H), 2.61 (m, 2 H), 2.31 (m, 2 H), 1.95 (s, 3 H), 1.83 (m, 2 H), 1.55-1.64 (m, 4 H). ¹³C NMR (75 MHz, CDCl3): δ = 199.8, 170.9, 153.5, 150.1, 139.1, 138.6, 127.7, 117.2, 113.5, 110.2, 95.8, 91.0, 65.6, 58.7, 54.4, 37.5, 32.6, 32.3, 26.6, 26.3, 20.8. MS: m/e = 558 [M+ - 2CO], 530 [M+ - 3CO], 446 [M+ - 5CO]. HRMS: m/e calcd for C26H24Co2O10 [M - 2CO+]: 558.0106; found: 558.0117.

22

Compound 8a: IR (KBr): νmax = 2930, 2087, 2046, 2017 cm. ¹H NMR (500 MHz, CDCl3): δ = 7.20 (d, J = 2.7 Hz, 1 H), 7.04 (d, J = 8.4 Hz, 1 H), 6.84 (dd, J = 8.4, 2.7 Hz, 1 H), 3.85 (s, 3 H), 3.20 (s, 2 H), 2.33-2.38 (m, 2 H), 2.26-2.30 (m, 2 H), 1.73-1.78 (m, 2 H), 1.66-1.72 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.0, 159.0, 139.1, 137.2, 130.1, 129.9, 129.3, 117.4, 113.6, 94.9, 89.5, 55.3, 42.1, 33.7, 30.5, 23.0, 22.7. MS: m/e = 510 [M+], 482 [M+ - CO], 454 [M+ - 2CO], 426 [M+ - 3CO], 398 [M+ - 4CO]. HRMS: m/e calcd for C22H16Co2O7 [M - CO+]: 481.9611; found: 481.9634.
Compound 8a′: IR (KBr): νmax = 2933, 2087, 2046, 2017 cm. ¹H NMR (500 MHz, CDCl3): δ = 7.28 (dd, obscured, 1 H), 7.23 (apparent t, J = 7.8 Hz, 1 H), 6.90 (dd, J = 8.0, 1.1 Hz, 1 H), 3.86 (s, 3 H), 3.33 (s, 2 H), 2.30-2.38 (m, 4 H), 1.73-1.79 (m, 2 H), 1.65-1.71 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.1, 155.8, 139.5, 137.5, 130.8, 127.5, 125.3, 124.7, 110.5, 95.1, 89.9, 55.9, 33.7, 32.2, 30.4, 23.0, 22.7. MS: m/e = 510 [M+], 482 [M+ - CO], 454 [M+ - 2CO], 426 [M+ - 3CO], 398 [M+ - 4CO]. HRMS: m/e calcd for C22H16Co2O7 [M+ - CO]: 481.9611; found: 481.9624.
Compound 8b: IR (KBr): νmax = 2964, 2085, 2046, 2026 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.92 (d, J = 8.9 Hz, 1 H), 6.75 (d, J = 8.9 Hz, 1 H), 3.87 (s, 3 H), 3.82 (s, 3 H), 3.34 (s, 2 H), 2.29-2.37 (m, 4 H), 1.73-1.79 (m, 2 H), 1.65-1.72 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.5, 153.9, 150.2, 136.2, 131.4, 127.3, 126.5, 112.0, 108.6, 95.9, 84.7, 56.6, 54.7, 33.5, 32.7, 30.5, 23.0, 22.6. MS: m/e = 512 [M+ - CO], 484 [M+ - 2CO], 428 [M+ - 4CO]. HRMS: m/e calcd for C23H18Co2O8: 539.9666; found: 539.9669.
Compound 8c: IR (KBr): νmax = 2935, 2085, 2043, 2012 cm. ¹H NMR (500 MHz, CDCl3): δ = 7.13 (s, 1 H), 6.64 (s, 1 H), 3.92 (s, 6 H), 3.19 (s, 2 H), 2.34-2.39 (m, 2 H), 2.26-2.31 (m, 2 H), 1.74-1.79 (m, 2 H), 1.68-1.73 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.1, 149.2, 148.4, 136.3, 130.4, 129.7, 114.6, 112.3, 95.1, 90.5, 56.0, 42.6, 33.8, 30.5, 23.0, 22.7. HRMS: m/e calcd for C23H18Co2O8 [M+ - CO]: 511.9716; found: 511.9711.
Compound 8d: IR (KBr): νmax = 2936, 2085, 2045, 2016 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.98 (s, 1 H), 3.92 (s, 3 H), 3.89 (s, 3 H), 3.88 (s, 3 H), 3.25 (s, 2 H), 2.36 (m, 2 H), 2.31 (m, 2 H), 1.77 (m, 2 H), 1.70 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.1, 152.4, 150.4, 142.8, 137.0, 133.7, 130.8, 123.3, 111.0, 95.2, 90.3, 61.6, 60.8, 56.0, 33.7, 32.8, 30.4, 23.0, 22.7. MS: m/e = 458 [M+ - 4CO], 430 [M+ - 5CO], 402 [M+ - 6CO]. HRMS: m/e calcd for C24H20Co2O9 [M+ - CO]: 541.9822; found: 541.9821.
Compound 8e: IR (KBr): νmax = 2931, 2084, 2049, 2015, 1638 cm. ¹H NMR (500 MHz, CDCl3): δ = 7.14 (apparent t, J = 7.7 Hz, 2 H), 7.09 (s, 1 H), 7.06 (t, J = 6.9 Hz, 1 H), 6.89 (d, J = 8.2 Hz, 2 H), 5.32 (s, 1 H), 3.98 (s, 3 H), 3.92 (s, 3 H), 3.86 (s, 3 H), 2.63-2.72 (m, 1 H), 2.50-2.60 (m, 1 H), 2.27-2.48 (m, 2 H), 1.82-1.95 (m, 2 H), 1.68-1.77 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 199.7, 152.7, 151.6, 142.8, 141.0, 138.3, 132.7, 131.4, 128.4, 126.8, 126.3, 125.0, 112.2, 91.6, 61.7, 60.8, 55.7, 47.6, 35.8, 31.4, 23.4, 22.8. MS: m/e = 562 [M+ - 3CO], 534 [M+ - 4CO], 478 [M+ - 6CO]. HRMS: m/e calcd for C30H24Co2O9 [M+ - 3CO]: 562.0237; found: 562.0240.
Compound 8f: IR (KBr): νmax = 2938, 2087, 2048, 2019 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.99 (s, 1 H), 3.91 (s, 3 H), 3.89 (s, 3 H), 3.85 (s, 3 H), 3.48 (s, 2 H), 2.71 (m, 2 H), 2.56 (m, 2 H), 2.06 (apparent quin, J = 7.5 Hz, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 199.7, 152.3, 150.8, 142.9, 141.5, 135.2, 133.4, 121.5, 112.2, 90.9, 87.9, 61.2, 60.8, 55.9, 39.2, 35.4, 27.4, 22.5. MS: m/e = 472 [M+ - 3CO], 444 [M+ - 4CO], 416 [M+ - 5CO], 388 [M+ - 6CO]. HRMS: m/e calcd for C23H18Co2O9 [M+ - CO]: 527.9654; found: 527.9666.
Compound 8g: IR (KBr): νmax = 2937, 2085, 2051, 2029 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.92 (d, J = 8.9 Hz, 1 H), 6.74 (d, J = 8.9 Hz, 1 H), 3.86 (s, 3 H), 3.81 (s, 3 H), 3.40 (s, 2 H), 2.76 (m, 1 H), 2.51-2.57 (m, 4 H), 2.29 (m, 1 H), 1.75-1.81 (m, 2 H), 1.61-1.72 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.0, 153.8, 150.1, 141.6, 136.7, 130.9, 126.7, 112.2, 108.5, 97.6, 56.8, 54.6, 38.5, 35.5, 34.6, 31.4, 29.7, 26.2. MS: m/e = 526 [M+ - CO], 498 [M+ - 2CO], 442 [M+ - 4CO]. HRMS: m/e calcd for C24H20Co2O8 [M+]: 553.9822; found: 553.9802.
Compound 8h: IR (KBr): νmax = 2918, 2085, 2046, 2016 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.97 (s, 1 H), 3.92 (s, 3 H), 3.89 (s, 3 H), 3.87 (s, 3 H), 3.31 (s, 2 H), 2.56 (m, 4 H), 1.79 (m, 2 H), 1.65 (m, 2 H), 1.59 (m, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 200.1, 152.4, 150.3, 142.89, 142.85, 136.3, 133.5, 123.3, 110.7, 97.1, 90.9, 61.7, 60.9, 56.0, 39.0, 35.4, 34.9, 31.6, 26.24, 26.19. MS: m/e = 584 [M+], 556 [M+ - CO], 528 [M+ - 2CO], 500 [M+ - 3CO], 472 [M+ - 4CO], 444 [M+ - 5CO], 414 [M+ - 6CO]. HRMS: m/e calcd for C25H22Co2O9 [M+ - 2CO]: 528.0029; found: 528.0030.
Compound 10: IR (KBr): νmax = 3035, 2919, 1607, 1516 cm. ¹H NMR (500 MHz, CDCl3): δ = 6.66 (s, 1 H), 6.65 (s, 1 H), 6.64 (s, 1 H), 6.60 (s, 1 H), 3.861 (s, 3 H), 3.860 (s, 6 H), 3.85 (s, 3 H), 2.86 (apparent t, J = 13.1 Hz, 1 H), 2.76 (dd, J = 14.2, 10.6 Hz, 1 H), 2.62-2.75 (m, 3 H), 2.61 (dd, J = 14.2, 6.9 Hz, 1H), 2.32 (d, J = 14.2 Hz, 1 H), 1.97 (m, 1 H), 1.89 (m, 1 H), 1.80 (m, 1 H), 0.95-1.75 (m, 22 H). ¹³C NMR (75 MHz, CDCl3): δ = 146.51, 146.45, 146.44, 146.3, 135.4, 135.1, 134.3, 113.8, 113.1, 112.5, 112.4, 56.00, 55.95, 55.90, 48.5, 43.9, 43.7, 38.0, 36.3, 35.8, 35.4, 34.9, 26.7, 26.4. MS: m/e = 260 [M+]. HRMS: m/e calcd for C17H24O2: 260.1776; found: 260.1775.

23

Typical Experimental Procedure
To a solution of 1f (0.406 g, mmol) in CH2Cl2 (9 mL) at 0 ˚C was added BF3˙OEt2 (25 µL, 0.20 mmol). After stirring for 45 min, aq NH4Cl was added and the mixture subjected to a conventional extractive workup (CH2Cl2). Flash chromatography (PE-Et2O = 1:1) afforded 8f (0.0319 g, 87% yield) as a viscous red-brown oil.