Benzoic Acid → Herkinorin

HRID 12321

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([OH:19])[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4].[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:18][C@H:17]([O:19][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:16](=[O:20])[C@H:15]2[C@@:6]1([CH3:28])[CH2:7][CH2:8][C@@H:9]1[C@:14]2([CH3:21])[CH2:13][C@@H:12]([C:22]2[CH:26]=[CH:25][O:24][CH:23]=2)[O:11][C:10]1=[O:27])=[O:4]

Participants

Reactant 2

HCID 243Benzoic Acid

HCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

Product 1

HCID 11431898HerkinorinYield 75%

Procedure

Compound 35 was synthesized using a procedure similar to that described in Example 29 from 8a using benzoic acid to afford 0.19 g (75%) of 35 as a white crystalline solid, mp 223-225° C.; 1H NMR (CDCl3): δ 1.13 (3H, s); 1.40 (1H, dd, J=11.6, 13.1); 1.50 (3H, s); 1.64 (2H, m); 1.84 (1H, dd, J=2.9, 11.3); 2.10 (2H, m); 2.37 (1H, ddd, J=3.0, 4.2, 12.3); 2.45 (1H, m); 2.50 (1H, m); 2.62 (1H, s); 3.01 (1H, dd, J=4.4, 12.5); 3.73 (3H, s); 5.00 (1H, dd, J=3.0, 3.0); 5.52 (1H, dd, J=4.7, 11.4); 6.32 (1H, dd, J=0.8, 2.0); 7.32 (1H, m); 7.36 (1H, dd, J=1.8, 1.8); 7.50 (2H, m); 7.65 (1H, tt, J=1.6, 7.5); 8.03 (2H, m); 13C NMR (CDCl3): δ15.6, 16.2, 18.3, 31.3, 35.2, 38.9, 43.4, 43.6, 51.4, 51.4, 52.1, 61.8, 72.2, 77.5, 108.5, 125.7, 129.0, 129.0, 129.9, 134.1, 139.3, 143.8, 165.4, 171.4, 172.2, 204.8; anal. C 67.85%, H 6.14%, O 25.70%, calcd for C28H30O8, C 68.00%, H 6.11%, O 25.88%.

Workup

customCompound 35 was synthesized

Sources & evidence

ORD record: ord-7c61a93160c64737938cc31ec6c2a77d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728001B2

Linked notes

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