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Original title:
Photochemische Differenzierung stereotoper Vinylgruppen und ihre Anwendung in der Totalsynthese von Punctaporonin C 
Translated title:
Photochemical differentiation of stereotopic vinyl groups and their application in the total synthesis of the natural product Punctaporonin C 
Year:
2008 
Document type:
Dissertation 
Institution:
Fakultät für Chemie 
Advisor:
Prof. Dr. Thorsten Bach 
Language:
de 
Subject group:
CHE Chemie 
Keywords:
[2+2]-Photocycloaddition, Totalsynthese, Punctaporonin C 
Translated keywords:
[2+2]-Photocycloaddition, Total Synthesis, Punctaporonin C 
TUM classification:
CHE 625d ; CHE 624d 
Abstract:
Thema der vorliegenden Arbeit war die photochemische Differenzierung zweier stereotoper Vinylgruppen in einer [2+2]-Photocycloaddition. Als Testsubstrate dienten verschieden substituierte 2,5-Divinylcyclopentyltetronate. Durch Variation von Lösungsmittel, Temperatur und Druck konnten die tetracyclischen Produkte in guten Ausbeuten (62-91%) und mit hohen Selektivitäten erhalten werden. Die Ergebnisse der Untersuchungen wurden in der ersten Totalsynthese von (±)-Punctaporonin C angewendet. Ausgehe...    »
 
Translated abstract:
In this thesis a photochemical differentiation of two stereotopic vinyl groups in a [2+2]-photocycloaddition was investigated. Various substituted 2,5-divinylcyclopentyltetronates were used as substrates. By variation of temperature and pressure as well as solvents, the tetracyclic products could be obtained in good yields (62-91%) and with high selectivity. The results of these studies were applied to the first total synthesis of (±)-Punctaporonin C. Starting with 7-tert-butoxynorbornadiene the...    »
 
Controlled terms:
Punctaporonin C ; Totalsynthese ; Vinylgruppe ; Photocycloaddition 
Last change:
13.02.2014