Studies directed toward the synthesis of the eremantholides 1.Preparation of a ring a/b model system via a conjugate addition-acylation protocol

✍ Scribed by Robert K. Boeckman Jr.; Debra K. Heckendorn; Richard L. Chinn

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 283 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95532-1

✦ Synopsis

Synthesis of a model A/R ring subunit of eremantholide A (1) is described Our interest in the development of a general synthetic protocol for eremantholide A (11, a member of a small group of modified germacran olide sequiterpene lactones isolated by LeQuesne and coworkers, was stimulated both by the significant anti-tumor activity exhibited by 1 and its congeners and the stereochemical issues implicit in a synthetic approach to this novel class of natural substances. X Since five of the six chiral centers present in eremantholide A (1) reside in the dioxabicycld3.3.Olcctanone system which comprises the A/B ring subunit of 1, we initially addressed the problem poeed by this sterecchemical array by undertaking the construction of the model bicychc lactone 2 described herein.