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Synlett 2018; 29(12): 1617-1621
DOI: 10.1055/s-0037-1610178
DOI: 10.1055/s-0037-1610178
letter
Biomimetic Total Synthesis of Scabellone B
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)
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 productsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610178.
- Supporting Information
- NMR
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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.