Rotundone → delta-Guaiene

HRID 333582Notes

Reaction equation

HRID 333582 reaction equation
[CH3:1][C@@H:2]1[C:8]2[C:9]([CH2:11][C@H:12]([CH3:13])[C:7]=2[CH2:6][C@H:5]([C:14]([CH3:16])=[CH2:15])[CH2:4][CH2:3]1)=O.C[C@@H]1[C@H]2C(=C(C)CC[C@@H](C(C)=C)C2)[C@H](O)C1.C[C@@H]1[C@H]2C(=C(C)CC[C@@H](C(C)=C)C2)[C@@H](O)C1>>[CH3:13][C@@H:12]1[C@H:7]2[C:8](=[C:2]([CH3:1])[CH2:3][CH2:4][C@@H:5]([C:14]([CH3:16])=[CH2:15])[CH2:6]2)[CH2:9][CH2:11]1

Participants

4

Reactant 3

HCID 5321003RotundoneHCID 14779596HCID 14779596, compoundHCID 66615727HCID 66615727, compound

Product 1

HCID 94275delta-Guaiene

Procedure

GC-analysis: 15% α-bulnesene oxides, 1%/3-patchoulenone, 1.25% rotundone, 1.8% bulnesenone, 0.1% (1R,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (compound of formula I), 1.6% (1S,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (compound of formula I).

Sources & evidence

ORD record
ord-66d63a21e0b5416ea866620c1806287a
Source dataset
uspto-grants-2014_11
Patent number
US08883468B2

Reaction notes

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