Synthesis of (±)-3H-Epivincamine via a Rh(II)-Triggered Cyclization/Cycloaddition Cascade
A synthesis of (±)-3H-epivincamine is reported. Important steps include (1) a Rh(II)-catalyzed intramolecular [3+2]-cycloaddition of an α-diazo indolo amide, (2) a reductive ring opening of the cycloadduct, (3) a decarboethoxylation reaction, and (4) a base-induced keto-amide ring contraction.
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| Veröffentlicht in: | Organic letters 2007-08, Vol.9 (17), p.3249-3252 |
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| container_title | Organic letters |
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| creator | England, Dylan B Padwa, Albert |
| description | A synthesis of (±)-3H-epivincamine is reported. Important steps include (1) a Rh(II)-catalyzed intramolecular [3+2]-cycloaddition of an α-diazo indolo amide, (2) a reductive ring opening of the cycloadduct, (3) a decarboethoxylation reaction, and (4) a base-induced keto-amide ring contraction. |
| doi_str_mv | 10.1021/ol071173x |
| format | Article |
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| ispartof | Organic letters, 2007-08, Vol.9 (17), p.3249-3252 |
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| language | eng |
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| source | American Chemical Society; MEDLINE |
| subjects | Antihypertensive Agents - chemical synthesis Cyclization Rhodium - chemistry Vasodilator Agents - chemical synthesis Vincamine - chemical synthesis |
| title | Synthesis of (±)-3H-Epivincamine via a Rh(II)-Triggered Cyclization/Cycloaddition Cascade |
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