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Isoquinocycline A

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Isoquinocycline A
Category Antibiotics
Catalog number BBF-02157
CAS
Molecular Weight 618.63
Molecular Formula C33H34N2O10

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Isoquinocycline A is originally isolated from Str. aureofaciens. It has strong anti-mycobacterium activity.

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IUPAC Name (1S,16R,17R,19R)-16-[(2S,4S,5R,6S)-4,5-dihydroxy-5-(1-hydroxyethyl)-6-methyloxan-2-yl]oxy-3,10-dihydroxy-17-methylspiro[18-oxapentacyclo[15.2.1.02,15.04,13.06,11]icosa-2,4(13),6(11),7,9,14-hexaene-19,5'-3,6-dihydro-2H-pyrrolo[2,3-b]pyrrole]-5,12-dione
Canonical SMILES CC1C(C(CC(O1)OC2C3=CC4=C(C(=C3C5CC2(OC56C=C7CCN=C7N6)C)O)C(=O)C8=C(C4=O)C(=CC=C8)O)O)(C(C)O)O
InChI InChI=1S/C33H34N2O10/c1-13(36)33(42)14(2)43-22(10-21(33)38)44-29-18-9-17-25(26(39)16-5-4-6-20(37)24(16)27(17)40)28(41)23(18)19-12-31(29,3)45-32(19)11-15-7-8-34-30(15)35-32/h4-6,9,11,13-14,19,21-22,29,36-38,41-42H,7-8,10,12H2,1-3H3,(H,34,35)/t13?,14-,19-,21-,22-,29+,31+,32+,33-/m0/s1
InChI Key LHDJGLQULHMCSJ-NDVAIKQNSA-N
Appearance Bright Yellow Crystal
Antibiotic Activity Spectrum mycobacteria
1. Synthesis of the isoquinocycline-pyrrolopyrrole substructure
Jens Cordes, Klaus Harms, Ulrich Koert Org Lett. 2010 Sep 3;12(17):3808-11. doi: 10.1021/ol101500k.
The synthesis of the pyrrolopyrrole substructure of the isoquinocyclines is reported. The pentacyclic (CDEFG) substructure of isoquinocycline A and B, which contains an unusual 2,4,5,6-tetrahydropyrrolo[2,3-b]pyrrole (FG) connected via an N,O-spiro acetal to the anthraquinoid core of the isoquinocycline aglycon has been synthesized. Key steps were a nickel(0)-mediated hydrocyanation of an alkynone, the conversion of an O,O-acetal into an N,O-acetal, and an intramolecular amidine alkylation.
2. The imidato-alkenyllithium route for the synthesis of the isoquinocycline-pyrrolopyrrole substructure
M André Breuning, Klaus Harms, Ulrich Koert Org Lett. 2011 Mar 18;13(6):1402-5. doi: 10.1021/ol200085g. Epub 2011 Feb 21.
A convergent and effective synthesis of the pyrrolopyrrole substructure (CDEFG) of the isoquinocyclines is reported. A key step is a tin-lithium exchange of an imidato-alkenyltin compound (a ring G equivalent) and the subsequent acylation with a lactone. The resulting acetal is used successfully for the ring F closure to the pyrrolopyrrole. The sole formation of the isoquinocycline N,O-acetal epimer is in accordance with the proposed mechanism for the isomerization of quinocyclines to isoquinocyclines.

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