Formal Synthesis of (±)-Peduncularine: Use of the [3 + 2] Annulation of Allylic Silanes and Chlorosulfonyl Isocyanate

Autor:	Claudia W. Roberson, K. A. Woerpel
Rok vydání:	2000
Předmět:	Chlorosulfonyl isocyanate Allylic rearrangement Annulation Bicyclic molecule Chemistry Organic Chemistry Biochemistry Medicinal chemistry Silane chemistry.chemical_compound Formal synthesis Lactam Physical and Theoretical Chemistry Peduncularine
Zdroj:	Organic Letters. 2:621-623
ISSN:	1523-7052 1523-7060
Popis:	[reaction: see text] The formal synthesis of the alkaloid (+/-)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (+/-)-peduncularine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::adb1872a8f1c7e7122e7e7c7c6b334f3 https://doi.org/10.1021/ol9913744 Zobrazit plný text záznamu