Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A
Author | : Zhang Wang |
Publisher | : |
Total Pages | : |
Release | : 2011 |
ISBN-10 | : OCLC:867753668 |
ISBN-13 | : |
Rating | : 4/5 ( Downloads) |
Download or read book Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A written by Zhang Wang and published by . This book was released on 2011 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A.