Allylsilane-Terminated Approach to Calicheamicin Model Systems
- 1 January 1992
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1992 (09) , 766-768
- https://doi.org/10.1055/s-1992-21488
Abstract
An organometallic route to bicyclic enediynes using iron-, copper-, silicon-, and palladium-mediated reactions is reported. The key step involves a Lewis acid promted Sakurai reaction of a conjugated allylsilane 7, which proceeded regio- and stereo-specifically. The bicyclic cross-conjugated enediyne 10 (12,12-ethylenedioxy-8-methylenebicyclo[8.3.1]tridec-4-ene-2,6-diyne) represents a model compound for the DNA cleaving calicheamicins.Keywords
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