Indole-Diterpene Synthetic Studies: Total Synthesis of (−)-21-Isopentenylpaxilline
| Autor: | Amos B. Iii Smith, Haifeng Cui |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Indole test Ketone Stereochemistry Organic Chemistry Total synthesis General Medicine Ring (chemistry) Biochemistry Catalysis Terpene Inorganic Chemistry chemistry.chemical_compound chemistry Drug Discovery Indole synthesis 21-isopentenylpaxilline Physical and Theoretical Chemistry Diterpene |
| Zdroj: | Helvetica Chimica Acta. 86:3908-3938 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.200390328 |
| Popis: | An efficient, stereocontrolled total synthesis of the complex indole-diterpene alkaloid (−)-21-isopentenylpaxilline (1) has been achieved. Key elements of the synthesis include the stereocontrolled construction of the advanced eastern hemisphere (−)-68, involving a highly efficient union of the eastern and western fragments (−)-68 and 5 exploiting our 2-substituted indole synthesis, application of the Negishiπ cycloalkylation tactic as a new, potentially general protocol for the construction of ring C, and the fragmentation of a β,γ-epoxy ketone to introduce the tertiary OH group at C(13) in the indole diterpene skeleton. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text