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. 2010 Aug 20;12(16):3708-11.
doi: 10.1021/ol1015652.

Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction

Jing Xu  1 , Eduardo J E Caro-Diaz, Emmanuel A Theodorakis
Affiliations

Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction

Jing Xu et al. Org Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
Structures of englerin A, B and natural analogues
Scheme 1
Scheme 1
Proposed biosynthetic approach
Scheme 2
Scheme 2
Retrosynthetic Analysis
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
Scheme 6
Scheme 6
See this image and copyright information in PMC

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