Two-Phase Terpene Total Synthesis: Historical Perspective and Application to the Taxol® Problem

被引:135
作者
Ishihara, Yoshihiro [1 ]
Baran, Phil S. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
biomimetic synthesis; oxidation; pyramid; terpenoids; total synthesis; C-H BONDS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; SELECTIVE FUNCTIONALIZATION; STEREOCONTROLLED SYNTHESIS; CATALYTIC HYDROXYLATION; SATURATED-HYDROCARBONS; EUDESMANE TERPENES; CASCADE CATALYSIS; METHYL-GROUPS;
D O I
10.1055/s-0030-1258123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This account presents our laboratory's latest endeavors in C-sp3-H activation in the context of total synthesis, as well as a historical perspective of the field of C-sp3-H activation. Our viewpoints in using a two-phase terpene synthesis strategy and how known oxidative transformations could benefit an eventual biomimetic synthesis of Taxol (R) are discussed. 1 Introduction 2 C-sp3-H Functionalization: A Historical Perspective 3 Two-Phase Terpene Synthesis: Proof of Principle 4 A Two-Phase Approach to Taxol (R): Planning Stage 5 Heuristic Value of the Oxidation Pyramid 6 Taxol (R): Precedent and First Ruminations 7 Conclusions and Outlook
引用
收藏
页码:1733 / 1745
页数:13
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