Pseudosymmetry in Azabicyclo[2.1.1]hexanes. A Stereoselective Construction of the Bicyclic Core of Peduncularine

Autor:	Justin R. Ragains, Jeffrey D. Winkler
Rok vydání:	2006
Předmět:	Bridged Bicyclo Compounds Bicyclic molecule Fragmentation (mass spectrometry) Chemistry Stereochemistry Intramolecular force Organic Chemistry Stereoselectivity Physical and Theoretical Chemistry Biochemistry Peduncularine
Zdroj:	Organic Letters. 8:4437-4440
ISSN:	1523-7052 1523-7060
Popis:	Intramolecular photocycloaddition of 41 or its equivalent leads to the formation of photoadduct 25. While retro-Mannich fragmentation of the "b" bond in 25 leads to the formation of 44 (via 43), with the incorrect relative stereochemistry for the synthesis of peduncularine 5, selective fragmentation of the "a" bond in 25 leads to the formation of 42 (via 26) with the correct relative stereochemistry for the synthesis of 5.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c83fbe1efaaca399dcaf86bace306cac https://doi.org/10.1021/ol061577+ Zobrazit plný text záznamu