An examination of π-facial selectivity in the diels-alder reaction of a chiral diene - a synthesis of (+)-5,6,10-tri-(EPI)-Actinobolin.

✍ Scribed by Alan P. Kozikowski; Thaddeus R. Nieduzak; James P. Springer

• Book ID: 104218223
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 296 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84109-x

✦ Synopsis

Sumaaryz The r-facial course of the Diels-Alder reaction of an Lthreonine derived silyloxydiene has been examined during the course of a study aimed at the total synthesis of actinobolin/bactobolin.

Actinobolin is an antibiotic of unusually low toxicity which possesses a broad spectrum of antibiotic activity.la It was first isolated as its crystalline sulfate salt by Haskell and Bartz in 1959.1brc Bactobolin, a closely related chlorine containing antibiotic, has been isolated fran a culture broth of Pseudomonas BtG 13-14.2a Bactobolin has been shown to prolong the survival period of mice implanted with mouse leukemia L-1210 cells.2b

In our efforts to synthesize these canpounds, we were intrigued with the following dissection in which an "intermolecular" DielsAlder reaction between a threonine-derived silyloxydiene and a Schenel. A Retrosynthetic Analysis.