74 海洋産の抗腫瘍性物質Bryostatin 1の全合成研究

概要

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Bryostatin 1 (1) is a marine antineoplastic substace isolated from the sea-mat Bugula neritina (Linne). Progress toward a total synthesis of (1) is to be presented. (1) was dissected into four fragments A, B, C, and D. Homochiral fragment A (12) was obtained from 2,2-dimethyl-1,3-proponediol via 21 steps, incorporating the asymmetric epoxidation-Red Al reductive ring opening methodology. Corey's methodology for the addition of cuprates to vinyl iodide was used to construct the 1,4-diene system of fragment B (14). The coupling of fragments A and B has been completed via the reaction between (17) and (18) in rather long steps and low yield. However shorter and efficient route (12+14) is under way. Fragment C (22) was synthsized by stereoselective acidic catalyzed epoxide opening of epoxy-urethane intermediate. The one of the chiral centers in fragment D (26) was provided by a metal chelation methodology. This strategy was also utilized to construct a fragment C-D (27).
天然有機化合物討論会の論文
1986-09-09