IT1241147B - Procedimento di preparazione di intermedi aciclici enantiomericamente puri utili per la sintesi della porzione lattonica di compactina, mevinolina e derivati - Google Patents

Info

Publication number

IT1241147B

IT1241147B IT20338A IT2033890A IT1241147B IT 1241147 B IT1241147 B IT 1241147B IT 20338 A IT20338 A IT 20338A IT 2033890 A IT2033890 A IT 2033890A IT 1241147 B IT1241147 B IT 1241147B

Authority

IT

Italy

Prior art keywords

compound

formula

image

derivatives

group

Prior art date

1990-05-17

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• 238000000034 method Methods 0.000 title abstract 2
• 238000002360 preparation method Methods 0.000 title abstract 2
• VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 title 1
• AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 title 1
• 125000002015 acyclic group Chemical group 0.000 title 1
• 230000015572 biosynthetic process Effects 0.000 title 1
• 239000000543 intermediate Substances 0.000 title 1
• 150000002596 lactones Chemical class 0.000 title 1
• AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 title 1
• BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 title 1
• 238000003786 synthesis reaction Methods 0.000 title 1
• 150000001875 compounds Chemical class 0.000 abstract 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
• 238000006243 chemical reaction Methods 0.000 abstract 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
• DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 abstract 1
• MUZIZEZCKKMZRT-UHFFFAOYSA-N 1,2-dithiolane Chemical group C1CSSC1 MUZIZEZCKKMZRT-UHFFFAOYSA-N 0.000 abstract 1
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 abstract 1
• FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
• 239000002841 Lewis acid Substances 0.000 abstract 1
• -1 acetate ester Chemical class 0.000 abstract 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
• 125000004185 ester group Chemical group 0.000 abstract 1
• 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
• 230000007062 hydrolysis Effects 0.000 abstract 1
• 238000006460 hydrolysis reaction Methods 0.000 abstract 1
• 150000007517 lewis acids Chemical class 0.000 abstract 1
• 238000011916 stereoselective reduction Methods 0.000 abstract 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
• 230000009466 transformation Effects 0.000 abstract 1