Wittig reactions of maleimide-derived stabilized ylides with alkyl pyruvates: concise approach to methyl ester of (+/-)-chaetogline A
| Title | Wittig reactions of maleimide-derived stabilized ylides with alkyl pyruvates: concise approach to methyl ester of (+/-)-chaetogline A |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Shelar, SV, Argade, NP |
| Journal | Synthesis-Stuttgart |
| Volume | 53 |
| Issue | 16 |
| Date Published | APR |
| Type of Article | Article |
| ISSN | 0039-7881 |
| Keywords | Amino acid, chaetogline A, dehydrative cyclization, maleimide, methyl pyruvate, Natural product, Wittig reaction |
| Abstract | A facile synthesis of methyl ester of chaetogline A is reported starting from the corresponding methyl 1-methyltryptophanate-derived- maleimide. A stereoselective Wittig olefination with a carbonyl function in methyl pyruvate followed by phosphorous pentoxide-induced- regioselective dehydrative cyclization are the essential reactions. An acid-induced thermodynamically driven stereoselective beta- to alpha-position migration of the exocyclic C=C bond unit in ethyl tetrahydroindolizinoindolylidenepropanoate is described. |
| DOI | 10.1055/a-1477-6043, Early Access Date = APR 2021 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.675 |
Divison category:
Organic Chemistry
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