HCID 54587249, compound → [8-(Furan-3-yl)-3,5-dihydroxy-2a,5a,6a,7-tetramethyl-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2H,3H-cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-6-yl]acetic acid

HRID 1087801Notes

Reaction equation

HRID 1087801 reaction equation
C/C=C(\C([O:7][C@@H:8]1[C@:16]2([CH3:38])[C@@H:17]([CH2:33][C:34]([O:36]C)=[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(C)=O)[CH2:9]1)=O)/C>[OH-].[Na+].CO>[CH3:31][C:23]1[C@H:24]([C:26]2[CH:27]=[CH:28][O:29][CH:30]=2)[CH2:25][C@H:21]2[O:20][C@@H:19]3[C@@H:14]4[O:13][CH2:12][C@@:11]5([CH3:39])[C@H:15]4[C@:16]([CH3:38])([C@@H:8]([OH:7])[CH2:9][C@H:10]5[OH:40])[C@@H:17]([CH2:33][C:34]([OH:36])=[O:35])[C@:18]3([CH3:32])[C:22]=12

Participants

4

Reactant 1

HCID 54587249HCID 54587249, compound

Product 1

HCID 185704[8-(Furan-3-yl)-3,5-dihydroxy-2a,5a,6a,7-tetramethyl-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2H,3H-cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-6-yl]acetic acidYield 69.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Salannic acid (1c) was prepared by a modification of the method of de Silva et al. (1969), supra. Salannin (30 mg, 0.050 mmol) was dissolved in 2.0 mL of 0.5 N NaOH in 50% aqueous methanol and incubated at 60° C. for 6 h. The reaction mixture was poured onto 10 mL of 0.5 N HC1 and extracted three times with 10-mL portions of diethyl ether. The organic layers were combined, washed once with 10 mL of saturated aqueous sodium chloride, and rotary evaporated in vacuo. Purification of the crude product by silica gel preparative HPLC (solvent = isopropanol-n-hexane acetic acid, 10:90:1) yielded salannic acid (16 mg). The IR spectrum of salannic acid showed the loss of the absorptions at 1710, 1655, and 735 cm-1, assigned to the tigloyl group (Henderson et al., 1968; Butterworth, J. H., et al. J. Chem. Soc.. Perkin Trans. I. 1972, 1445-2450; Yamasaki and Klocke, unpublished data), and the appearance of a very broad, intense absorption at 3400 cm-1 characteristic of a carboxylic acid (Silverstein et al., Spectrometric Identification of Organic Compounds, 4th ed. Wiley, New York, 1981, pp. 204-208). All of the 1H-NMR absorptions of the tigloyl (δ1.81, 1.94, and 6.96), acetyl (δ1.94, and carbomethoxyl (δ3.24) groups had vanished.

Workup

  1. customSalannic acid (1c) was prepared by a modification of the method of de Silva et al. (1969), supra
  2. additionThe reaction mixture was poured onto 10 mL of 0.5 N HC1
  3. extractionextracted three times with 10-mL portions of diethyl ether
  4. washwashed once with 10 mL of saturated aqueous sodium chloride
  5. customrotary evaporated in vacuo
  6. customPurification of the crude product by silica gel preparative HPLC (solvent = isopropanol-n-hexane acetic acid, 10:90:1)

Sources & evidence

ORD record
ord-18a4a127f47341138a79f7bc38cdb8c1
Source dataset
uspto-grants-1990_10
Patent number
US04960791

Reaction notes

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