1381848-54-9Relevant articles and documents
Total Synthesis of Polycavernosides A and B, Two Lethal Toxins from Red Alga
Iwasaki, Kotaro,Sasaki, Satori,Kasai, Yusuke,Kawashima, Yuki,Sasaki, Shohei,Ito, Takanori,Yotsu-Yamashita, Mari,Sasaki, Makoto
, p. 13204 - 13219 (2017)
Polycavernosides A and B are glycosidic macrolide natural products isolated as the toxins causing fatal human poisoning by the edible red alga Gracilaria edulis (Polycavernosa tsudai). Total synthesis of polycavernosides A and B has been achieved via a convergent approach. The synthesis of the macrolactone core structure is highlighted by the catalytic asymmetric syntheses of the two key fragments using hetero-Diels-Alder reaction and Kiyooka aldol reaction as the key steps, their union through Suzuki-Miyaura coupling, and Keck macrolactonization. Finally, glycosylation with the l-fucosyl-d-xylose unit and construction of the polyene side chain through Stille coupling completed the total synthesis of polycavernosides A and B.
Total synthesis of (-)-polycavernoside A: Suzuki-Miyaura coupling approach
Kasai, Yusuke,Ito, Takanori,Sasaki, Makoto
supporting information; experimental part, p. 3186 - 3189 (2012/08/28)
A total synthesis of (-)-polycavernoside A, a marine lethal toxin isolated from the edible alga Gracilaria edulis, has been achieved via a convergent approach. The synthesis is highlighted by catalytic asymmetric syntheses of the two key fragments and their union through Suzuki-Miyaura coupling and Keck macrolactonization.