Structure via PubChem · Public domain (PubChem)
isomigrastatin
Sign in to saveIsomigrastatin is an analogue of migrastatin, an organic compound that naturally occurs in the Streptomyces platensis bacteria. Isomigrastatin has shown promise as a drug in the treatment of cancer. A laboratory synthesis was reported in 2007. ==Synthesis== ===Total synthesis=== Migrastatin synthesis is a precursor of isomigrastatin. In order to synthesize isomigrastatin, reagent 11 and 15 need to be prepared. Through LACDAC reaction, Luche reduction, aqueous Ferrier rearrangement and Epoxidation, reagent 6, 7, 8, 9, 10 are synthesized to 11. Aldehyde 12 reacts is alkyldenated by Witting reage
Chemical data
- Formula
- C27H39NO7
- Molecular weight
- 489.6 g/mol
- IUPAC name
- 4-[(E,5S)-7-[(2R,3S,4S,5S,6E,10E)-4-hydroxy-5-methoxy-3-methyl-12-oxo-1-oxacyclododeca-6,10-dien-2-yl]-5-methyl-4-oxooct-6-enyl]piperidine-2,6-dione
- SMILES
- C[C@H]1[C@@H]([C@H](/C=C/CC/C=C/C(=O)O[C@H]1/C(=C/[C@H](C)C(=O)CCCC2CC(=O)NC(=O)C2)/C)OC)O
- InChIKey
- TYTDEHCAAKKYOG-FEJRZXFSSA-N
- XLogP
- 2.8
- Polar surface area
- 119 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 489.272652588
Show 4 more facts
- isomeric SMILES
- C[C@H]([C@H](/[C@@](C)=C/[C@@H](C(CCCC2CC(NC(C2)=O)=O)=O)C)O1)[C@H](O)[C@@H](OC)/C=C/CC/C=C/C1=O
- chemical formula
- C₂₇H₃₉NO₇
- Commons category
- Isomigrastatin
- canonical SMILES
- COC1C=CCCC=CC(=O)OC(C(C)=CC(C)C(=O)CCCC2CC(=O)NC(=O)C2)C(C)C1O
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Synthesis
- Total synthesis
- Biosynthesis
- References
Isomigrastatin is an analogue of migrastatin, an organic compound that naturally occurs in the Streptomyces platensis bacteria. Isomigrastatin has shown promise as a drug in the treatment of cancer. A laboratory synthesis was reported in 2007. ==Synthesis== ===Total synthesis=== Migrastatin synthesis is a precursor of isomigrastatin. In order to synthesize isomigrastatin, reagent 11 and 15 need to be prepared. Through LACDAC reaction, Luche reduction, aqueous Ferrier rearrangement and Epoxidation, reagent 6, 7, 8, 9, 10 are synthesized to 11. Aldehyde 12 reacts is alkyldenated by Witting reagent 13 to make 14, and 14 is hydrogenated to afford 15. thumb|left|600px
Fragment coupling of intermediate 11 and 15 would be the next step. Using lithium borohydride, lactol arrangement of reagent 11 is reduced to create alcohol 16 which could be converted to 17 as well. Coupled with phosphorane 15, reagent 16 and 17 are oxidized to synthesize aldehyde 18. thumb|left|600px
Excerpted from Wikipedia’s “isomigrastatin” article, available under the CC BY-SA 4.0 licence.