File:Complete synthesis.svg
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Summary
| Description |
English: Visual representation of the synthesis of Gambierol. The tetracyclic acetic acid and tetracyclic alcohol together, form the octacyclic backbone of gambierol. Stille coupling of compound 8 to dienyl stannane (9) results in the active, toxic form of gambierol.Reaction conditions: (a) Dimethyldioxirane, CH2Cl2, -78 to 0 °C; DIBAL, CH2Cl2, 90% (10:1 mixture). (b) TPAP, NMO, 4 Å MS, CH2Cl2, rt, 97%. (c) imidazole, toluene, 110 °C, 100% (4:1 mix of 14:15). (d) CSA, MeOH, 0 °C, 90%. (e) Zn(OTf)2, EtSH, CH2Cl2, rt, 91%. (f) Ph3SnH, AIBN, toluene, 110 °C, 95%. (g) TPAP, NMO, 4 Å MS, CH2Cl2, rt, 98%. (h) CHI3, PPh3. KOt-Bu, 0 °C, 95%. (i) Zn-Cu couple, MeOH, AcOH, 0 °C, 85%. (j) SiF4, CH3CN, CH2Cl2, 0 °C, 89%. (k) 18, Pd2dba3‚CHCl3, P(furyl)3, CuI, DMSO, 40 °C, 75%.6 |
| Date | |
| Source | Own work |
| Author | Myrthe |
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File history
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| Date/Time | Thumbnail | Dimensions | User | Comment | |
|---|---|---|---|---|---|
| current | 11:58, 16 March 2017 | | 512 × 967 (222 KB) | Gambierol | User created page with UploadWizard |
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