ChemicalBook CAS DataBase List BORRELIDIN

BORRELIDIN synthesis

13synthesis methods

Product Name:BORRELIDIN
CAS Number:7184-60-3
Molecular formula:C28H43NO6
Molecular Weight:489.64

1,2-Cyclopentanedicarboxylic acid, 4-oxo-, 1,2-diMethyl ester, (1R,2R)-

35079-19-7
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7184-60-3
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$125.00/500μg

Yield:-

Steps:

Multi-step reaction with 29 steps
1.1: 72 percent / SnCl₄ / CH₂Cl₂ / 8 h / 0 - 25 °C
2.1: 92 percent / Raney Ni / methanol / 3 h / Heating
3.1: 92 percent / LiAlH₄ / diethyl ether / 12 h / 25 °C
4.1: 84 percent / imidazole; DMAP / CH₂Cl₂ / 8 h / 25 °C
5.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C
6.1: toluene / 1 h / -78 °C
6.2: NaH / tetrahydrofuran / 1 h / 0 °C
6.3: TBAI / tetrahydrofuran / 12 h / 25 °C
7.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C
8.1: 93 percent / iPr₂NEt / CH₂Cl₂ / 8 h / 0 - 25 °C
9.1: OsO₄; NMO; pyridine / acetone; H₂O / 12 h / 25 °C
9.2: 91 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 25 °C
10.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
10.2: 77 percent / tetrahydrofuran / 2 h / -78 °C
11.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C
12.1: 91 percent / DDQ / CH₂Cl₂ / 1 h / 25 °C / pH 7.0
13.1: 93 percent / imidazole; DMAP / CH₂Cl₂ / 8 h / 40 °C
14.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C
14.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C
15.1: Ph₂S / sunlight
16.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C
17.1: 89 percent / DDQ / H₂O; CH₂Cl₂ / 0.5 h / 25 °C / pH 7.0
18.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 2 h / 25 °C
19.1: BF₃*OEt₂ / tetrahydrofuran / 1 h / -78 °C
20.1: 86 percent / iPr₂NEt / CH₂Cl₂ / 12 h / 25 °C
21.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C
22.1: 83 percent / CF₃COOH / CH₂Cl₂ / 3 h / 0 °C
23.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C
23.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C
24.1: hydroquinone; nBu₃SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C
24.2: 54 percent / I₂ / CH₂Cl₂ / 25 °C
25.1: 90 percent / CuI / Pd(PPh₃)4 / toluene / 8 h / 80 °C
26.1: 69 percent / Me₂BBr / CH₂Cl₂ / 2 h / -78 °C
27.1: 85 percent / TEMPO; TCCA / CH₂Cl₂ / 1 h / 25 °C
28.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 0.5 h / 25 °C
29.1: NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C