Hydrogen Peroxide → (+)-Sclareol oxide

HRID 844589Notes

Reaction equation

[CH3:1][C@@:2]12[C@@H:11]([CH2:12][CH2:13][C@@:14]([OH:18])([CH:16]=C)C)[C@@:10](O)([CH3:19])[CH2:9][CH2:8][C@H:7]1[C:6]([CH3:22])([CH3:21])[CH2:5][CH2:4][CH2:3]2.O=[O+][O-].OO>>[CH3:16][C:14]1[O:18][C@@:2]2([CH3:1])[C@@H:11]([C@:10]3([CH3:19])[C@@H:5]([CH2:4][CH2:3]2)[C:6]([CH3:21])([CH3:22])[CH2:7][CH2:8][CH2:9]3)[CH2:12][CH:13]=1

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 24823Ozone

HCID 163263Sclareol

Product 1

HCID 7057250(+)-Sclareol oxide

Procedure

Sclareol is oxidised with ozone, followed by treatment with alkaline hydrogen peroxide to give sclareol oxide. The sclareol oxide is then oxidised with an organic hydroperoxide, preferably tert-butyl hydroperoxide, to give 12-acetyl-norlabdane oxide. The 12-acetyl-norlabdane oxide is converted to 12-acetoxy-norlabdane oxide by oxidation with an organic peracid, preferably peracetic acid. The 12-acetoxy-norlabdane oxide is then reduced to norlabdane oxide with sodium borohydride in the presence of a transition metal salt. The reaction scheme of EP 0882191A may be represented as follows:

Sources & evidence

ORD record: ord-a407cabda3864302b15b12f89c1edef1
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380404B1

Reaction notes

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