Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.
نویسندگان
چکیده
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.
منابع مشابه
Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.
An efficient formal synthesis of (-)-englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell-lines. Our enantioselective strategy involved the construction of the BC ring system of compound 1 through a Rh(II)-catalyzed [4+3] cycloaddition reaction followed by subsequent attachment ...
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ورودعنوان ژورنال:
- Organic letters
دوره 12 16 شماره
صفحات -
تاریخ انتشار 2010