Catalytic Activity Studies
of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes
for the Syntheses of Herbarumin I and Stagonolide A

Debendra K. Mohapatra; R. Somaiah; M. Mallikarjuna Rao; Fréderic Caijo; Marc Mauduit; J. S. Yadav

doi:10.1055/s-0029-1219807

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Synlett 2010(8): 1223-1226
DOI: 10.1055/s-0029-1219807

LETTER

Catalytic Activity Studies of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes for the Syntheses of Herbarumin I and Stagonolide A

Debendra K. Mohapatra*^a, R. Somaiah^a, M. Mallikarjuna Rao^a, Fréderic Caijo^b, Marc Mauduit*^b, J. S. Yadav*^a
^a Organic Chemistry Division-I, Indian Institute of Chemical Technology (CSIR), Uppal Road, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: mohapatra@iict.res.in;
^b Ωcat SYSTEM®, Ecole Nationale Supérieure de Chimie de Rennes, Av. Du Général Leclerc, 35700 Rennes, France

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Publication History

Received 2 March 2010
Publication Date:
09 April 2010 (online)

Abstract
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Abstract

The catalytic activity of four aminocarbonyl group containing ‘boomerang’-type ring-closing metathesis catalysts have been studied for ten-membered lactone and compared well with the Grubbs I and II as well as the Hoveyda-Grubbs catalysts. The activity was found to be superior to the above three ring-closing metathesis catalysts and suggesting novel stereoselective total syntheses of herbarumin I and stagonolide A.

Key words

decanolides - stagonolides - herbarumin I - Wittig reaction - ring-closing metathesis

Supporting Information

References and Notes

1a Dräger G. Kirschning A. Thiericke R. Zerlin M. Nat. Prod. Rep. 1996, 13: 365

Google Scholar
1b Ferraz HMC. Bombonato FI. Longo LS. Synthesis 2007, 3261

Google Scholar
1c Riatto VB. Pilli RA. Victor MM. Tetrahedron 2008, 64: 2279

Google Scholar
2 Yuzikhin O. Metino G. Berestetskiy A. J. Agric. Food Chem. 2007, 55: 7707

Crossref PubMed Google Scholar
3a Evidente A. Lanzetta R. Capasso R. Andolfi A. Vurro M. Zonno MC. Phytochemistry 1995, 40: 1637

Google Scholar
3b Evidente A. Capasso R. Andolfi A. Bottallico A. Vurro M. Zonno MC. Phytochemistry 1997, 44: 1041

Google Scholar
3c Evidente A. Capasso R. Andolfi A. Vurro M. Zonno MC. Phytochemistry 1998, 48: 941

Google Scholar
4a Evidente A. Lanzetta R. Capasso R. Vurro M. Bottalico A. Phytochemistry 1993, 34: 999

Google Scholar
4b Evidente A. Capasso R. Bouzeid MA. Lanzetta R. Vurro M. Bottalico A. J. Nat. Prod. 1993, 56: 1937

Google Scholar
5 Arnone A. Assante G. Montorsi M. Nasini G. Ragg E. Gazz. Chim. Ital. 1993, 123: 71

Google Scholar
6a Rivero-Cruz JF. Macias M. Gerda-Garcia-Rojas CM. Mata R. Tetrahedron 2000, 56: 5337

Google Scholar
6b Rivero-Cruz JF. Macias M. Gerda-Garcia-Rojas CM. Mata R. J. Nat. Prod. 2003, 66: 511

Google Scholar
7a Fürstner A. Radkowski K. Chem. Commun. 2001, 671

Google Scholar
7b Fürstner A. Radkowski K. Wirtz C. Goddard R. Lehmann WC. Mynott R. J. Am. Chem. Soc. 2002, 124: 7061

Google Scholar
7c Sabino AA. Pilli RA. Tetrahedron Lett. 2002, 43: 2819

Google Scholar
7d Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Helv. Chim. Acta 2003, 86: 3717

Google Scholar
7e Gurjar MK. Karmakar S. Mohapatra DK. Tetrahedron Lett. 2004, 45: 4525

Google Scholar
7f Nanda S. Tetrahedron Lett. 2005, 46: 3661

Google Scholar
7g Gurjar MK. Nagaprasad R. Ramana CV. Karmakar S. Mohapatra DK. ARKIVOC 2005, (iii): 237

Google Scholar
7h Salaskar A. Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry 2006, 17: 325

Google Scholar
7i Boruwa J. Gogoi N. Barua NC. Org. Biomol. Chem. 2006, 4: 3521

Google Scholar
7j Gupta P. Kumar P. Tetrahedron: Asymmetry 2007, 18: 1688

Google Scholar
7k Nagaiah K. Sreenu D. Rao RS. Yadav JS. Tetrahedron Lett. 2007, 48: 7173

Google Scholar
7l Yadav JS. Kumar VN. Rao RS. Srihari P. Synthesis 2008, 1938

Google Scholar
7m Yadav JS. Ather H. Gayathri KU. Rao NV. Prasad AR. Synthesis 2008, 3945

Google Scholar
7n Selvam JJP. Rajesh K. Suresh V. Babu DC. Venkateswarlu Y. Tetrahedron: Asymmetry 2009, 20: 1115

Google Scholar
7o Kamal A. Venkata Reddy P. Prabhakar S. Tetrahedron: Asymmetry 2009, 20: 1120

Google Scholar
8a Evidente A. Cimmino A. Berestetskiy A. Mitina G. Andolfi A. Motta A. J. Nat. Prod. 2008, 71: 31

Google Scholar
8b Evidente A. Cimmino A. Berestetskiy A. Andolfi A. Motta A. J. Nat. Prod. 2008, 71: 1897

Google Scholar
9a Grubbs RH. Chang S. Tetrahedron 1998, 54: 4413

Google Scholar
9b Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371

Google Scholar
9c Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012

Google Scholar
9d Maier ME. Angew. Chem. Int. Ed. 2000, 39: 2073

Google Scholar
9e Nevalainen M. Koskinen AMP. Angew. Chem. Int. Ed. 2001, 40: 4060

Google Scholar
9f Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18

Google Scholar
9g Prunet J. Angew. Chem. Int. Ed. 2003, 42: 2826

Google Scholar
9h Love JA. In Handbook of Metathesis Grubbs RH. Wiley-VCH; Weinheim: 2003. p.296-322

Google Scholar
9i Grubbs RH. Tetrahedron 2004, 60: 7117

Google Scholar
9j Deiters A. Martin SF. Chem. Rev. 2004, 104: 2199

Google Scholar
9k Gradillas A. Pérez-Castells J. Angew. Chem. Int. Ed. 2006, 45: 6086

Google Scholar
10a Rix D. Caijo F. Laurent I. Gulajski L. Grela K. Mauduit M. Chem. Commun. 2007, 3771

Google Scholar
10b Rix D. Caijo F. Laurent I. Boeda F. Clavier H. Nolan SP. Mauduit M. J. Org. Chem. 2008, 73: 4225

Google Scholar
10c Clavier H. Caijo F. Borré E. Rix D. Boeda F. Nolan SP. Mauduit M. Eur. J. Org. Chem. 2009, 4254

Google Scholar
11 Srihari P. Kumaraswamy B. Rao GM. Yadav JS. Tetrahedron: Asymmetry 2010, 21: 106

Crossref Google Scholar
12 Kirihata M. Ohe M. Ichimoto I. Ueda H. Biosci. Biotech. Biochem. 1992, 56: 1825

Crossref Google Scholar
13 Freeman F. Robarge KD. Carbohydr. Res. 1986, 154: 270

Crossref Google Scholar
16a Nicolaou KC. Seitz SP. Pavia MR. Petasis NA. J. Org. Chem. 1979, 44: 4011

Google Scholar
16b Hayward CM. Yohannes D. Danishefsky SJ. J. Am. Chem. Soc. 1993, 115: 9345

Google Scholar
19a Corey EJ. Gras JL. Ulrisch P. Tetrahedron Lett. 1976, 17: 809

Google Scholar
19b Bhatt MV. Kulkarni SV. Synthesis 1983, 249

Google Scholar

14

Analytical and Spectral Data of 10
[α]_D ^²5 +7.6 (c 1.1, CHCl₃). IR (neat): 3455, 2924, 2852, 2097, 1461 cm^-¹. ^¹H NMR (300 MHz, CDCl₃): δ = 7.43-7.19 (m, 5 H), 6.05 (m, 1 H), 5.34 (dd, J = 17.3, 1.5 Hz, 1 H), 5.18 (dd, J = 10.6, 1.5 Hz, 1 H), 4.60 (ABq, J = 13.6, 11.3 Hz, 2 H), 4.31 (t, J = 5.3 Hz, 1 H), 3.74 (m, 1 H), 3.25 (t, J = 6.04 Hz, 1 H), 2.90 (br s, 1 H), 2.59 (br s, 1 H), 1.69-1.24 (m, 4 H), 0.92 (t, J = 6.8 Hz, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 137.7, 137.9, 137.7, 128.4, 127.8, 128.1, 116.1, 84.2, 73.9, 73.7, 72.6, 35.3, 18.8, 14.0. HRMS: m/z calcd for C₁₅H₂₂O₃Na: 273.1466; found: 273.1472.

15

Analytical and Spectral Data of 11
[α]_D ^²5 +27.0 (c 0.7, CHCl₃). IR (neat): ν_max = 3398, 2963, 2925, 2855, 1723, 1711, 1639, 1461, 1129 cm^-¹. ^¹H NMR (300 MHz, CDCl₃): δ = 7.38-7.23 (m, 5 H), 6.02-5.68 (m,
2 H), 5.29-5.12 (m, 2 H), 5.07-4.95 (m, 2 H), 4.66 (ABq, J = 17.2, 11.5 Hz, 2 H), 4.21-4.06 (m, 2 H), 3.50 (t, J = 4.7 Hz, 1 H), 2.33-2.24 (m, 2 H), 2.14-2.06 (dd, J = 7.4, 6.9 Hz, 2 H), 1.78-1.63 (m, 4 H), 1.40-1.22 (m, 2 H), 0.96-0.84 (m, 12 H), 0.07 (s, 3 H), 0.04 (s, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 172.7, 138.5, 138.1, 137.6, 128.2, 127.8, 127.5, 116.5, 115.3, 83.9, 74.6, 74.0, 73.7, 34.9, 33.7, 33.1, 31.5, 25.8, 24.1, 18.7, 14.0, -4.2, -5.0. HRMS: m/z calcd for C₂₇H₄₄O₄NaSi: 483.2906; found: 483.2914.

17

Analytical and Spectral Data of 12
[α]_D ^²5 +18.2 (c 1.0, CHCl₃). IR (film): ν_max = 4272, 3801, 3471, 2954, 1722, 1641, 1371, 1217, 1091 cm^-¹. ^¹H NMR (300 MHz, CDCl₃): δ = 7.40-7.30 (m, 5 H), 5.68-5.57 (m, 1 H), 5.50 (dd, J = 15.7, 1.1 Hz, 1 H), 5.21 (dt, J = 9.5, 1.1 Hz, 1 H), 4.73-4.53 (m, 3 H), 3.37 (dd, J = 9.6, 1.9 Hz, 1 H), 2.34-2.27 (m, 2 H), 2.03-1.78 (m, 4 H), 1.49 (m, 1 H), 1.36-1.22 (m, 4 H), 0.89 (t, J = 7.4 Hz, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 175.5, 137.3, 133.1, 130.3, 128.5, 128.0, 124.6, 80.9, 72.3, 68.8, 68.8, 34.5, 33.6, 33.5, 24.5, 17.8, 13.9. HRMS: m/z calcd for C₁₉H₂₆O₄Na: 341.1728; found: 341.1722.

18

General Procedure for the Metathesis Reaction
To a stirred solution of diene (1.0 mmol) in freshly prepared dry CH₂Cl₂ (200 mL) at r.t. was added the metathesis catalyst (0.01 mmol) under argon. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (EtOAc-hexane = 1:6) to afford the E-isomer as the sole product.

20

Analytical and Spectral Data of 2
[α]_D ^²5 +10.6 (c 1.0, EtOH); lit.:^7b [α]_D ^²0 +10.8 (c 0.51, EtOH). ^¹H NMR (300 MHz, CDCl₃): δ = 5.61 (d, J = 15.9 Hz, 1 H), 5.49 (m, 1 H), 4.95 (td, J = 9.4, 2.2 Hz, 1 H), 4.42 (br s, 1 H), 3.51 (d, J = 9.8 Hz, 1 H), 2.76 (br s, 1 H), 2.45-2.25 (m, 2 H), 2.06-1.81 (m, 4 H), 1.56 (m, 1 H), 1.43-1.18 (m, 3 H), 0.91 (t, J = 7.3 Hz, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 176.3, 130.7, 124.6, 73.6, 73.3, 70.1, 34.4, 33.6, 33.3, 24.6, 17.9, 13.8. IR (neat): ν_max = 3455, 3038, 2955, 2920, 2867, 1711, 1639, 1219 cm^-¹. HRMS: m/z calcd for C₁₂H₂₀O₄Na: 251.1259; found: 251.1264.

21

Analytical and Spectral Data of 1
Mp 71-72 ˚C; [α]_D ^²5 -59.2 (c 0.5, EtOH). ^¹H NMR (300 MHz, CDCl₃): δ = 6.42 (d, J = 16.0 Hz, 1 H), 6.32 (m, 1 H), 4.65 (dt, J = 9.5, 2.4 Hz, 1 H), 4.05 (dd, J = 9.5, 6.2 Hz, 1 H), 3.57 (d, J = 6.2 Hz, 1 H), 2.57-2.41 (m, 2 H), 2.20-1.90 (m, 6 H), 1.43-1.18 (m, 3 H), 0.93 (t, J = 7.2 Hz, 3 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 199.5, 174.2, 143.1, 131.9, 76.5, 74.4, 34.2, 34.0, 33.5, 24.9, 18.0, 13.7. IR (neat): ν_max = 3468, 2925, 1740, 1700, 1638, 1219 cm^-¹. HRMS: m/z calcd for C₁₂H₁₉O₄: 227.1278; found: 227.1274.

Supplementary Material

Supporting Information