Part I. Synthetic studies of furanosesquiterpenoid tetrahydrolinderazulenes. Total synthesis of (plusmn)-echinofuran, and, Part II. Synthetic applications of chiral furyl boronates. Asymmetric synthesis of optically pure substituted furylamines.

摘要

The furanosesquiterpenoid echinofuran (41) was isolated by Higa and co-workers in 1987 from the gorgonian Echinogorgia praelonga . This compound shows bioactivity to inhibit 90% of the cell division of fertilized sea urchin eggs at 1 μg/ml.; In Chapter 1, a brief introduction of the syntheses and synthetic applications of 3,4-disubstituted furans is given. An overview of the isolation, structure elucidation and bioactivities of echinofuran (41) is then presented. In addition, various synthetic approaches and total syntheses toward furanosesquiterpenoids are reviewed.; Chapter 2 concerns the aim of our research work, retrosynthetic analysis and strategy. Herein we report the syntheses of the 5,7,5-tricyclic molecules 97 and 144 by employing an organosilicon-organoboron protocol developed in our laboratory. Compound 144 served as the pivotal precursor to realize the total synthesis of echinofuran (41). In addition, some model studies of furan cyclization are also discussed.; In Chapter 3, a brief conclusion is provided.