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Synlett 2018; 29(12): 1617-1621
DOI: 10.1055/s-0037-1610178
letter
© Georg Thieme Verlag Stuttgart · New York

Biomimetic Total Synthesis of Scabellone B

Tao Yu
Department of Chemistry and Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi’an 710127, P. R. of China   Email: xiangdonghu@nwu.edu.cn
,
Xin Shu
Department of Chemistry and Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi’an 710127, P. R. of China   Email: xiangdonghu@nwu.edu.cn
,
Kewu Yang
Department of Chemistry and Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi’an 710127, P. R. of China   Email: xiangdonghu@nwu.edu.cn
,
Xiangdong Hu*
Department of Chemistry and Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi’an 710127, P. R. of China   Email: xiangdonghu@nwu.edu.cn
› Author Affiliations
The project is supported by the National Natural Science Foundation of China (21772153, 21642006), the Key Science and Technology ­Innovation Team of Shaanxi Province (2017KCT-37), and the China Postdoctoral Science Foundation (334100041).

Further Information

Publication History

Received: 03 March 2018

Accepted after revision: 15 May 2018

Publication Date:
18 June 2018 (online)

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Abstract

A biomimetic total synthesis of scabellone B is described. Through sequential regioselective introduction of a geranyl group by means of silyl protection, oxidative dimerization, and biomimetic oxo-6π electrocyclization with good cyclization selectivity, a biomimetic ­approach to scabellone B was achieved in five steps and 32% overall yield.

Key words

total synthesis - protecting groups - dimerization - electrocyclic reactions - natural products

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610178.
  • Supporting Information
  • NMR
 

  • References and Notes

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  • 10 Scabellone BEt3N (47 mg, 0.54 mmol) was added to solution of biquinone 6 (100 mg, 0.18 mmol) in CH2Cl2 (5 mL), and the mixture was stirred for 5 min. The mixture was then concentrated by vacuum and purified by column chromatography (silica gel) to give a purple oil; yield: 95 mg (95%); Rf = 0.3 (EtOAc–PE, 1:5). IR (CCl4): 3467, 2922, 1684, 1594, 1221, 750 cm–1. 1H NMR (400 MHz, CDCl3): δ = 6.40 (s, 1 H), 6.00 (d, J = 8 Hz, 1 H), 5.79 (s, 1 H), 5.50 (s, 1 H), 5.27 (d, J = 8 Hz, 1 H), 5.05 (m, 1 H), 5.00 (t, J = 4 Hz, 1 H), 4.93 (t, J = 4 Hz, 1 H), 3.88 (s, 3 H), 3.79 (s, 3 H), 3.57 (m, 1 H), 3.36 (dd, J = 12 Hz, 1 H), 1.94–1.98 (m, 4 H), 1.92–1.94 (m, 2 H), 1.92 (s, 3 H), 1.85–1.87 (m, 2 H), 1.62 (s, 3 H), 1.59 (s, 3 H), 1.56 (s, 3 H), 1.50 (s, 3 H), 1.49 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 182.7, 178.9, 158.0, 151.5, 150.2, 144.5, 139.3, 137.7, 137.2, 131.9, 131.8, 130.9, 127.0, 124.4, 124.0, 123.7, 117.0, 111.2, 107.4, 98.5, 67.8, 56.3, 56.2, 40.0, 39.9, 26.7, 26.5, 26.3, 25.7, 25.7, 17.7, 17.6, 17.4, 16.7. HRMS (ESI+): m/z [M + H]+ calcd for C34H43O6, 547.3054; found: 547.3041.