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ChemicalBook CAS DataBase List 12-DEOXYPHORBOL 13-PHENYLACETATE
58821-98-0

12-DEOXYPHORBOL 13-PHENYLACETATE synthesis

3synthesis methods
Benzeneacetic acid, (3aR,3bS,6aR,9aS,9bR,10R,11aS)-3,3a,3b,6,6a,7,9a,9b,10,11-decahydro-6a,9b-dihydroxy-5-(hydroxymethyl)-3,3,8,10-tetramethyl-7-oxo-11aH-azuleno[5,4-e]indazol-11a-yl ester

1035455-45-8
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Yield:58821-98-0 87%

Reaction Conditions:

in ethyl acetate;benzene at 20; for 0.75 h;UV-irradiation;

Steps:

10

Example 10; Formation of Cyclopropane Ring Structure; A solution of S10 (5.4 mg, 10.9 μmol) in benzene/EtOAc (1:1, 1 mL) was stirred at room temperature in a disposable glass vial flushed with argon. The solution was irradiated with UV light (300 nm) using a Rayonet photochemical reactor at room temperature for 45 min. until TLC indicated complete consumption of the starting material. The reaction mixture was concentrated under reduced pressure, and subjected to flash (100% EtOAc, ID 8 mm, 1 g silica) to give 12-deoxyphorbol-13-phenylacetate (DPP) as a white powder (4.4 mg, 87%). The product was characterized by:TLC Rf=0.45 (100% EtOAc), one black spot in p-anisaldehyde (visible under UV lamp)[α]D23=5+35.7° (c 0.44, CHCl3)1H NMR (500 MHz, CDCl3 after D2O shake): δ 7.57 (br s, 1H, C1-H), 7.35-7.24 (m, 5H, Ar-H), 5.63 (d, J=4.5 Hz, 1H, C7-H), 4.02 (d, J=12.8 Hz, 1H, C20-H), 3.94 (d, J=12.8 Hz, 1H, C20-H) 3.62 (d, J=14.7 Hz, 1H, CH2Ph), 3.58 (d, J=14.7 Hz, 1H, CH2Ph), 3.24 (dd, J=2.7, 2.7 Hz, 1H, C10-H), 2.94 (m, 1H, C8-H), 2.50 (d, J=19 Hz, 1H, C5-H), 2.43 (d, J=19 Hz, 1H, C5-H), 3.07 (dd, J=7.0, 14.0 Hz, 1H, C12-H), 1.99-1.95 (m, 1H, C11-H), 1.76 (dd, J=1.4, 2.9 Hz, 3H, C19-H), 1.54 (dd, J=11.1, 14.5 Hz, 1H, C12-H), 1.03 (br s, 6H, C16-H and C17-H), 0.86 (d, J=6.5 Hz, 3H, C18-H), 0.75 (d, J=5.4 Hz, 1H, C14-H) ppm.13C NMR (125 MHz, CDCl3): δ 209.4, 173.6, 161.4, 139.8, 133.2, 132.8, 130.2, 129.3 (2), 128.6 (2), 127.3, 76.1, 73.7, 68.2, 64.0, 55.7, 41.7, 39.1, 38.6, 36.3, 32.4, 31.7, 23.0, 22.9, 18.5, 15.3, 10.1 ppm.FT-IR (thin film): ν 3399, 2921, 1707, 1625, 1455, 1246, 1133, 1015 cm-1.HRMS: Calcd.: (for C28H34O6Na): 489.2253, Found: 489.2256

References:

US2009/187046,2009,A1 Location in patent:Page/Page column 15

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