Lovastatin → Lovastatin Acid

HRID 504055

Reaction equation

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

Participants

Reactant 2

HCID 53232Lovastatin

HCID 3225883,5-Dihydroxypentanoic acid

Product 1

HCID 64727Lovastatin Acid

Procedure

For example, lovastatin (Ia) is prepared by lactonisation of the 3,5-dihydroxy pentanoic acid derivative (II) to (Ia) either by heating in an organic solvent or in the presence of an acid catalyst. The former, viz. mevinolinic acid, is obtained from a fermentation broth containing Asperigillus Terreus.

Workup

temperatureby heating in an organic solvent or in the presence of an acid catalyst

Sources & evidence

ORD record: ord-5c4d68f7bdef48c8b8ecd2e2f3a1a222
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07777056B2

Linked notes

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