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Synthesis of the Carbon Framework of Scholarisine A by Intramolecular Oxidative Coupling
Author(s) -
Watanabe Tsugunori,
Umezawa Naoki,
Kato Nobuki,
Higuchi Tsunehiko
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203454
Subject(s) - intramolecular force , oxidative coupling of methane , indole test , chemistry , monoterpene , oxidative phosphorylation , stereochemistry , indole alkaloid , organic chemistry , catalysis , biochemistry
Scholarisine A, isolated from the leaves of Alstonia scholaris , 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 N ‐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.