Synlett 2010(12): 1733-1745  
DOI: 10.1055/s-0030-1258123
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

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

Yoshihiro Ishihara, Phil S. Baran*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA
Fax: +1(858)7847375; e-Mail: pbaran@scripps.edu;
Further Information

Publication History

Received 18 June 2010
Publication Date:
01 July 2010 (eFirst)

Abstract

This account presents our laboratory’s latest endeavors in Csp3−H activation in the context of total synthesis, as well as a historical perspective of the field of Csp3−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® are discussed.

1 Introduction

2 Csp3−H Functionalization: A Historical Perspective

3 Two-Phase Terpene Synthesis: Proof of Principle

4 A Two-Phase Approach to Taxol®: Planning Stage

5 Heuristic Value of the Oxidation Pyramid

6 Taxol®: Precedent and First Ruminations

7 Conclusions and Outlook