37 抗腫瘍活性ジテルペン・アフィディコリンの高効率的合成(口頭発表の部)

抄録

Aphidicolin (1), isolated from the fungus Cepharosporium aphididicola, is an antibiotics that shows marked activity against Herpes simplex Type I virus. In addition to its antifeedant property, aphidicolin (1) exhibits a considerable antitumor activity. Herein we report conceptually distinct two access to 1 featuring (i) successive intramolecular Diels-Alder reactions and (ii) intramolecular Heck reaction and intramolecular Diels-Alder reaction as the key steps. (i) First Generation Synthesis of 1 via the Successive Intramolecular Diels-Alder Reactions Formal synthesis of aphidicolin (1) has been achieved by means of the successive Diels-Alder reactions (5→6 and 13→14) as the key steps of the first generation synthesis of aphidicolin (1). (II) Second generation Synthesis of 1 by Intramolecular Heck Reaction and Intramolecular Diels-Alder Reaction Intramolecular Heck reaction of the bromide (19) and intramolecular Diels-Alder reaction of the triene (13) have been utilized as the key steps for 13-step formal total synthesis of (±)-aphidicolin (1).