A Stereospecific Transannular Diels-Alder Approach to the [6.6.7] Tricyclic Skeleton Related to Aphidicolin and Scopadulan Natural Products
- 1 September 1995
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1995 (09) , 1081-1088
- https://doi.org/10.1055/s-1995-4077
Abstract
Model trans-cis-cis (TCC) macrocyclic triene 7 was synthesized using a convergent approach. Upon heating at 200°C, a 1,5-hydrogen-shift on the diene moiety was found to compete with the transannular Diels-Alder (TADA) reaction, thus leading to a mixture of tricyclic products. However, the diene rearrangement could be avoided by using boron trifluoride-diethyl ether complex as catalyst at reduced temperature (60°C). The exclusive formation of the trans-syn-cis [6.6.7] (TSC) tricyclic product 8 through an endo approach was observed. This result demonstrates the feasibility of a TADA strategy for synthesizing the title compounds and analogs.Keywords
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