Total Syntheses of Dysidealactams E and F and Dysidealactone B, Drimane-Type Sesquiterpenes Derived from a Dysidea sp. of Marine Sponge

Yuhao Chen; Ping Lan; Lorenzo V. White; Weiguang Yang; Martin G. Banwell

doi:10.1055/a-2002-8680

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(12): 1529-1533
DOI: 10.1055/a-2002-8680

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Special Issue Honoring Masahiro Murakami’s Contributions to Science

Total Syntheses of Dysidealactams E and F and Dysidealactone B, Drimane-Type Sesquiterpenes Derived from a Dysidea sp. of Marine Sponge

Authors

Yuhao Chen

^aGuangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong, 524023, P. R. of China
Ping Lan

^bInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, P. R. of China
Lorenzo V. White

^bInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, P. R. of China
Weiguang Yang∗

^aGuangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong, 524023, P. R. of China
Martin G. Banwell ∗

^aGuangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong, 524023, P. R. of China

^bInstitute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Dedicated to Professor Masahiro Murakami (Kyoto University) in recognition of his profound and ingenious contributions to so many aspects of chemical synthesis.

Abstract

Dysidealactams E and F and dysidealactone B are recently reported marine natural products. Their syntheses from β-cyclocitral are detailed here. The preparation of certain derivatives and analogues of these compounds is also described and single-crystal X-ray analyses of two of these, as well as that of (±)-dysidealactam F, are reported.

Key words

cycloaddition - drimanes - marine natural products - sesquiterpenes - total synthesis

Volltext

Referenzen

References and Notes

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16 (±)-[(5aS,9aS)-6,6,9a-Trimethyl-1,3-dioxo-1,3,4,5,5a,6,7,8,9,9a-decahydro-2H-benzo[e]isoindol-2-yl]acetic acid [(±)-4] A Schlenk tube equipped with a magnetic stirrer bar was charged with compound (±)-8 (500 mg, 2.01 mmol), glycine (1.51 g, 20.1 mmol), and 1:1 MeCN–H₂O (6.0 mL). The tube was sealed and the contents were heated at 105 °C (oil-bath temperature) for 8 h. The cooled mixture was then diluted with H₂O (10 mL) and the separated aqueous phase was extracted with EtOAc (3 × 25 mL). The combined organic phases were dried (Na₂SO₄), filtered, and concentrated under reduced pressure and the resulting residue was subjected to flash chromatography [silica gel, EtOAc–PE (1:3 + 1% AcOH)] to afford, after concentration of the appropriate fractions, a clear yellow oil; yield: 331 mg (54%); R_f = 0.3 (1:3 EtOAc–PE +1% AcOH). FTIR (ATR): 2930, 1703, 1420, 1391, 1233, 1207, 1117, 937, 735 cm^–1. ¹H NMR (400 MHz, CD₃OD): δ = 4.13 (s, 2 H), 2.50 (d, J = 14.0 Hz, 2 H), 2.25 (m, 1 H), 1.97 (m, 1 H), 1.76 (m, 1 H), 1.63–1.45 (complex m, 3 H), 1.38–1.25 (complex m, 3 H), 1.23 (s, 3 H), 0.96 (s, 3 H), 0.93 (s, 3 H); COOH proton not observed. ¹³C{¹H} NMR (100 MHz, CD₃OD): δ = 171.8, 171.5, 170.9, 151.4, 141.5, 53.2, 42.9, 39.2, 37.6, 36.3, 34.4, 33.9, 23.0, 22.0, 21.1, 19.5, 19.0. HRMS (TOF ESI, +): m/z [M + H]⁺ calcd for C₁₇H₂₄NO₄: 306.1705; found: 306.1714.
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21 For a conceptually related approach using the naturally derived drimane polygodial, see: Rhak KJ, Bissember AC, Smith JA. Tetrahedron 2018; 74: 1167
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Zusatzmaterial

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