Asymmetric Synthesis of the Main Core of Kaurane Family Members Triggered by an Oxidative Polycyclization-Pinacol Tandem Process

作者：Desjardins Samuel; Maertens Gaetan; Canesi Sylvain^*

来源：Organic Letters, 2014, 16(18): 4928-4931.

DOI：10.1021/ol5024486

Polycyclization processes represent expeditious routes used in both nature and the laboratory to produce complex polycyclic molecules. A new stereoselective oxidative variant of such a polycyclization has been developed in which the cascade is triggered by a phenol dearomatization and is concluded by a pinacol transposition. This unprecedented avenue combines the synthetic power of a polycyclization and a transposition in tandem and enables the rapid formation of the tetracyclic main core of kaurane diterpenes containing several asymmetric and quaternary carbon centers in a single step from a simple phenol derivative.

• 出版日期2014-9-19