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Synlett 2012; 23(10): 1473-1476
DOI: 10.1055/s-0031-1290375
letter
© Georg Thieme Verlag Stuttgart · New York

Synthetic Utility of Sugar-Derived Cyclic Nitrones: A Diastereoselective Synthesis of Linear 4-Azatriquinanes

Anandaraju Bandaru
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India, Fax: +91(22)25723480   Email: kpk@chem.iitb.ac.in
,
Krishna P. Kaliappan*
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India, Fax: +91(22)25723480   Email: kpk@chem.iitb.ac.in
› Author Affiliations
Further Information

Publication History

Received: 02 February 2012

Accepted after revision: 12 April 2012

Publication Date:
29 May 2012 (online)

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Abstract

A diastereoselective Pauson–Khand reaction has been utilized as the key step in the construction of azatriquinanes from sugar-derived nitrones.

Key words

diastereoselectivity - sugar derivatives - nitrones - ­Pauson–Khand reaction

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
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  • References and Notes

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  • 14 Genaral Procedure for Pauson–Khand Reaction: To a stirred solution of enyne (1 mmol) in CH2Cl2 (30 mL), [Co2(CO)8] (1.2 mmol) was added under a nitrogen atmosphere at 25 °C. After stirring at 25 °C for 1 h, the solvent was removed to obtain the crude product. To a solution of the above crude product in toluene (20 mL), DMSO (10 mmol) was added and the solution was heated at reflux overnight at 80 °C. After completion, the reaction mixture was quenched with 1% HCl (50 mL) (except for compounds 33 and 34, which were quenched with water) and extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by basic alumina column chromatography. Data for (1S,2S,3S,8aS,8bS)-1,2-bis(benzyloxy)-3-(benzyloxymethyl)-1,2,3,8,8a,8b-hexahydrocyclo-penta[a]pyrrolizin-7(5H)-one (15): R f  = 0.4 (EtOAc–hexanes, 50%); [α] d 20 –9.8 (c 1.00, CHCl3); 1H NMR (CDCl3, 400 MHz): δ = 7.37–7.26 (m, 15 H), 6.0–5.99 (m, 1 H), 4.69–4.44 (m, 6 H), 4.08–4.02 (m, 3 H), 3.71 (d, J = 16.9 Hz, 1 H), 3.62 (dd, J = 9.4, 4.5 Hz, 1 H), 3.52 (dd, J = 9.4, 6.5 Hz, 1 H), 3.29–3.24 (m, 1 H), 3.19 (dd, J = 10.5, 3.3 Hz, 1 H), 3.12–3.08 (m, 1 H), 2.60 (dd, J = 17.6, 6.2 Hz, 1 H), 2.10 (dd, J = 17.6, 3.3 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ = 209.3, 186.9, 138.4, 138.1, 137.7, 128.7, 128.6, 128.5, 128.1, 128.0, 127.9, 127.8, 125.1, 86.8, 86.1, 73.6, 73.0, 72.7, 72.5, 72.3, 70.2, 54.2, 48.5, 40.6; IR (neat): 3872, 3030, 2924, 2854, 2109, 1966, 1703, 1646, 1454, 1367, 1306, 1215, 1106, 1028, 754, 698 cm–1; HRMS (ESI): calcd for C32H34NO4 [M + 1]+ 496.2488; found 496.2469