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Synlett 2018; 29(10): 1358-1361
DOI: 10.1055/s-0036-1591561
DOI: 10.1055/s-0036-1591561
letter
A Simple Aluminum Bromide-Promoted Diastereoselective Synthesis of Panduratin A Derivatives
Authors
This research was supported by the University of Malaya Research Grants (BKP044-2017 and RG392-17AFR).
Further Information
Publication History
Received: 19 January 2018
Accepted after revision: 13 March 2018
Publication Date:
11 April 2018 (online)
Abstract
A facile diastereoselective synthesis of panduratin A derivatives using commercially available aluminum(III) bromide is reported. The effect of substituents on the Diels–Alder reaction of various trans-chalcones with (E)-ocimene was investigated. A series of panduratin A derivatives were prepared in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591561.
- Supporting Information (PDF)
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References and Notes
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- 18 Panduratin A Derivatives 3a–r; General ProcedureA 1.0 M solution of AlBr3 in CH2Br2 (30 mol%) was added to a solution of the appropriate trans-chalcone (1 equiv) in anhyd toluene or CH2Cl2 (2 mL/mmol) at r.t. (28 °C) under N2. (E)-Ocimene (5 equiv) was added, and the mixture was stirred at r.t. for 24 h or until all the chalcone was consumed. The mixture was then poured into ice–water acidified with 3 N aq HCl to pH 2–3. The resulting mixture was extracted with EtOAc, and the organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 5–20% EtOAc–hexane).[3-Methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-en-1-yl](phenyl)methanone (3)Pale brown solid; yield: 124 mg (72%); mp 90–92 °C. 1H NMR (400 MHz, CDCl3): δ = 1.38 (s, 6 H), 1.70 (s, 3 H), 1.97–2.09 (m, 2 H), 2.11–2.18 (m, 1 H), 2.34–2.39 (m, 2 H), 3.36 (td, J = 10.5, 6.4 Hz, 1 H), 4.08 (dd, J = 10.5, 5.0 Hz, 1 H), 4.74 (t, J = 6.9 Hz, 1 H), 5.41 (br s, 1 H), 6.99 (t, J = 6.9 Hz, 1 H), 7.09–7.14 (m, 4 H), 7.32 (t, J = 7.8 Hz, 2 H), 7.40 (t, J = 7.3 Hz, 1 H), 7.79 (d, J = 7.8 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 17.7, 22.8, 25.6, 28.7, 35.0, 36.9, 42.8, 50.3, 121.3, 123.7, 125.7, 127.0, 127.9, 128.3, 128.4, 131.9, 132.5, 136.5, 137.4, 146.3, 200.6. HRMS (ESI): m/z [M + H]+ calcd for C25H29O: 345.2218; found: 345.2225.(2-Chlorophenyl)[3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-en-1-yl]methanone (3a)Yellow oil; yield: 32 mg (17%). 1H NMR (400 MHz, CDCl3): δ = 1.50 (s, 3 H), 1.58 (s, 3 H), 1.68 (s, 3 H), 2.11–2.22 (m, 2 H), 2.25–2.32 (m, 2 H), 2.39–2.46 (m, 1 H), 3.34 (td, J = 9.8, 7.1 Hz, 1 H), 3.96 (dd, J = 10.2, 4.2 Hz, 1 H), 4.97 (t, J = 6.6 Hz, 1 H), 5.40 (br s, 1 H), 7.04–7.08 (m, 1 H), 7.14–7.30 (m, 8 H). 13C NMR (100 MHz, CDCl3): δ = 18.0, 23.1, 25.8, 29.0, 33.8, 37.4, 40.6, 55.3, 121.0, 123.6, 126.0, 126.6, 127.7, 128.2, 129.4, 130.8, 131.5, 131.5, 132.0, 136.9, 139.0, 145.7, 202.7. HRMS (ESI): m/z [M + H]+ calcd for C25H28 35ClO: 379.1829; found: 379.1831.