A Convergent Total Synthesis of Epolactaene: An Application of the Bridgehead Oxiranyl Anion Strategy. -The key steps in the synthesis of epolactaene (XIa) and some analogues are formation of the silylated epoxylactone (VIII) and its aldol reaction with aldehydes. Direct silylation of the epoxylactone (II) can also be performed but in this case competitive dimerization takes place. Relative configuration of epoxylactones also affects the degree of dimerization resp. oligomerization which can be minimized by strict control of reaction conditions. The syn-epoxylactone (XII) gives considerable amounts of oligomers and low yields of the desired product. -(KURAMOCHI, K.; NAGATA, S.; ITAYA, H.; MATSUBARA, Y.; SUNOKI, T.; UCHIRO, H.; TAKAO, K.-I.; KOBAYASHI*, S.; Tetrahedron 59 (2003) 49, 9743-9758; Front. Res. Cent.
Die aus D‐Glucose leicht zugängliche Zwischenstufe (I) wird zum Aufbau chiraler Synthone (VIII), (XIII), (XVI) und (XVIII) unter Anwendung bekannter Verfahren herangezogen.
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