A novel route to the marasmane skeleton via a tandem rearrangement-cyclopropanation reaction. total synthesis of (+)-isovelleral
| Autor: | Joannes B. P. A. Wijnberg, Roel P. L. Bell, Aede de Groot |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Cyclopropanes Mesylates Polycyclic Sesquiterpenes Tandem Trimethylsilyl Cyclopropanation Stereochemistry Basidiomycota Organic Chemistry Total synthesis Organische Chemie Combinatorial chemistry chemistry.chemical_compound chemistry Indenes Isovelleral Yield (chemistry) Reagent Enol ether Life Science EPS Nuclear Magnetic Resonance Biomolecular Sesquiterpenes |
| Zdroj: | Journal of Organic Chemistry 66 (2001) 7 Journal of Organic Chemistry, 66(7), 2350-2357 |
| ISSN: | 0022-3263 |
| Popis: | A general and efficient route to the marasmane skeleton is described. Total syntheses of two simple marasmanes (35 and 37) in racemic form were achieved using a MgI2-catalyzed rearrangement−cyclopropanation reaction of trimethylsilyl enol ether 31 derived from naphthalenone 30. The reaction proceeds in high yield with complete diastereoselectivity and does not require the use of special cyclopropanation reagents. Application of this novel route to the marasmane framework was extended to the synthesis of naturally occurring (+)-isovelleral (41). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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