Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation

The Journal of Organic Chemistry
Jihoon Lee, James S Panek

Abstract

Complete details of an asymmetric synthesis of (+)-isatisine A (1) are described. The synthesis highlights the use of a highly diastereoselective Mukaiyama-type [3 + 2]-annulation of allylsilane 5 with the unsaturated aldehyde 9a to assemble the functionalized tetrahydrofuran core of isatisine A. A convergent route to the framework of the natural product was established that employed a substrate-controlled indole coupling that was followed by a late-stage intramolecular copper(I)-mediated amidation to complete the assembly of the tetracyclic framework of (+)-isatisine A. In addition, the scope of the [3 + 2]-annulation was evaluated and enhanced utilizing diastereomeric allylsilanes anti-5 and syn-5 to establish an efficient route to stereochemically well-defined tetrahydrofurans.

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Citations

Sep 26, 2015·Chemistry : a European Journal·Robert W FosterTom D Sheppard
Dec 18, 2018·Organic Letters·Christopher R WongJames S Panek
Apr 18, 2018·The Journal of Organic Chemistry·Bren Jordan P AtienzaF G West

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