HCID 54587249, compound → Methyl (2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)-3-(acetyloxy)-8-(3-furanyl)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2a,5a,6a,7-tetramethyl-5-(2-methyl-1-oxobutoxy)-2H,3H-cyclopenta[b]furo[2′,3′,4′:4,5]naphtho[2,3-d]furan-6-acetate

HRID 1087802Notes

Reaction equation

HRID 1087802 reaction equation
[CH3:1]/[CH:2]=[C:3](\[C:5]([O:7][C@@H:8]1[C@:16]2([CH3:38])[C@@H:17]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[C@:18]3([CH3:32])[C:22]4=[C:23]([CH3:31])[C@H:24]([C:26]5[CH:27]=[CH:28][O:29][CH:30]=5)[CH2:25][C@H:21]4[O:20][C@@H:19]3[C@H:14]3[C@H:15]2[C@:11]([CH3:39])([CH2:12][O:13]3)[C@H:10]([O:40][C:41]([CH3:43])=[O:42])[CH2:9]1)=[O:6])/[CH3:4]>C(O)C.[Pd]>[CH3:1][CH2:2][CH:3]([C:5]([O:7][C@@H:8]1[C@:16]2([CH3:38])[C@@H:17]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[C@:18]3([CH3:32])[C:22]4=[C:23]([CH3:31])[C@H:24]([C:26]5[CH:27]=[CH:28][O:29][CH:30]=5)[CH2:25][C@H:21]4[O:20][C@@H:19]3[C@H:14]3[C@H:15]2[C@:11]([CH3:39])([CH2:12][O:13]3)[C@H:10]([O:40][C:41]([CH3:43])=[O:42])[CH2:9]1)=[O:6])[CH3:4]

Participants

4

Reactant 1

HCID 54587249HCID 54587249, compound

Product 1

HCID 52952323Methyl (2aR,3R,5S,5aR,6R,6aR,8R,9aR,10aS,10bR,10cR)-3-(acetyloxy)-8-(3-furanyl)-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2a,5a,6a,7-tetramethyl-5-(2-methyl-1-oxobutoxy)-2H,3H-cyclopenta[b]furo[2′,3′,4′:4,5]naphtho[2,3-d]furan-6-acetateYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Salannin (25 mg., 0.041 mmol) in 0.5 ml of ethanol was stirred with 13 mg of 5% palladium on alumina at 25° C. under hydrogen (5 atm) for 15 min. The reaction mixture was then filtered and evaporated in vacuo. The residue was chromatographed by silica gel preparative HPLC (solvent = isopropanol-n-hexane, 2:23) to afford 2',3'-dihydrosalannin (19 mg): IR max (cm-1) 1735 (s), 1500 (w), 870 (m); 1H-NMR (CDC13) δ 0.95 (t, J =7.4 Hz, 1 H, 4' -Me), 0.96 (t, J =7.4 Hz, 2 H, 4' -Me), 1.23 (d, J =6.5 Hz, 2 H, 5' -Me), 1.30 (d, J =6.9 Hz, 1 H, 5' -Me), 1.45-1.70 (m, 2 H, H-3'ab), 1.75-1.95 (m, 1 H, H-2'), 2.07 (s, 3 H, 3-Ac), 3.60 (apparent br s, 2 H, H-28a,b), 4.87 (dd, J =2.9, 2.9 Hz, 1 H, H-3); EI-MS, m/z 598 (M+, 100%), 583 (M-CH3, 7), 567 (M-OCH3, 2), 513 (M-COCH(CH3) Ch2Ch3, 4), 504 (10), 496 (M-HOCOCH(CH3)CH2CH3, 5), 421 (17), 397 (5), 283 (30), 259 (23), 235 (17), 230 (9), 202 (9), 185 (9) 173 (14), 147 (13 ), 119 (8), 85 (CH3CH2CH(CH3)CO+, 14), 57 CH3CH2CH(CH3)+, 46).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated in vacuo
  3. customThe residue was chromatographed by silica gel preparative HPLC (solvent = isopropanol-n-hexane, 2:23)

Sources & evidence

ORD record
ord-5a400534e4414e908aef77ac7bcbf383
Source dataset
uspto-grants-1990_10
Patent number
US04960791

Reaction notes

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