An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation
摘要:
A concise synthesis of the polycycle 27, which incorporates the 5,5,7-tricyclic ring core of rameswaralide 1, using a biogenetically inspired acid-catalysed [4+3]-cycloaddition approach starting from the furano-butenolide 26 is described, namely, 26-28/29-27. Under thermal conditions, the same furanobutenolide 26 gives the alternative polycyclic compound 35, resulting from a [4+2]-cycloaddition involving the furan as dienophile. (C) 2009 Elsevier Ltd. All rights reserved.
An intramolecular [4+3]-cycloaddition approach to rameswaralide inspired by biosynthesis speculation
作者:Gerald Pattenden、Johan M. Winne
DOI:10.1016/j.tetlet.2009.10.046
日期:2009.12
A concise synthesis of the polycycle 27, which incorporates the 5,5,7-tricyclic ring core of rameswaralide 1, using a biogenetically inspired acid-catalysed [4+3]-cycloaddition approach starting from the furano-butenolide 26 is described, namely, 26-28/29-27. Under thermal conditions, the same furanobutenolide 26 gives the alternative polycyclic compound 35, resulting from a [4+2]-cycloaddition involving the furan as dienophile. (C) 2009 Elsevier Ltd. All rights reserved.