Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Org Lett. 2010 Aug 20;12(16):3708-11. doi: 10.1021/ol1015652.
An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.
本文报道了(-)-表海松烷 A(1)的对映选择性形式合成。该策略的关键是呋喃 10 和重氮酯 11 在 Rh 催化下的[4+3]环加成反应,该反应在分子内 aldol 缩合后,生成了表海松烷的三环支架。该策略还为具有生物重要性的愈创木烷倍半萜的核心基序提供了一种快速、高效和立体选择性的方法。