Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling. Issue 13 (11th February 2013)

• Record Type: Journal Article
• Authors: Watanabe, Tsugunori; Kato, Nobuki; Umezawa, Naoki; Higuchi, Tsunehiko
• Is Part Of: Chemistry. Volume 19:Issue 13(2013)
• Page Start: 4255
• Page End: 4261
• Publication Date: 2013-02-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201203454
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Scholarisine A, isolated from the leaves of <italic>Alstonia scholaris</italic>, is a monoterpene indole alkaloid with an unprecedented cage‐like structure. In this paper, preparation of the distinctive cage‐like core skeleton of scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10‐oxa‐tricyclo[5.3.1.0^{3, 8}]undecan‐9‐one structure fused with indolenine. Intramolecular oxidative coupling by using <italic>N</italic>‐iodosuccinimide gave the carbon framework of scholarisine A in moderate yield, which is the first example of intramolecular oxidative‐coupling reaction between non‐activated enolate and indole. This study lays the foundation for continued investigations towards the total synthesis of scholarisine A.</p> </abstract>