Tetrahedron

Synthesis of 3-hydroxyindolin-2-one alkaloids,(±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3- …

T Kawasaki, M Nagaoka, T Satoh, A Okamoto, R Ukon…

Index: Kawasaki, Tomomi; Nagaoka, Miyuki; Satoh, Tomoko; Okamoto, Ayako; Ukon, Rie; Ogawa, Atsuyo Tetrahedron, 2004 , vol. 60, # 15 p. 3493 - 3503

Full Text: HTML

Citation Number: 84

Abstract

Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3- hydroxyindolin-2-one alkaloids,(±)-donaxaridine, as well as (±)-convolutamydines A and E, was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones.

Related Articles:

Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives

[Kumar, Akshay; Chimni, Swapandeep Singh Beilstein Journal of Organic Chemistry, 2014 , vol. 10, p. 929 - 935]

Molecular sieve mediated decarboxylative Mannich and aldol reactions of β-ketoacids

[Zhong, Fangrui; Jiang, Chunhui; Yao, Weijun; Xu, Li-Wen; Lu, Yixin Tetrahedron Letters, 2013 , vol. 54, # 32 p. 4333 - 4336]

Condensations of Isatin with Acetone by the Knoevenagel Method1

[Braude; Lindwall Journal of the American Chemical Society, 1933 , vol. 55, p. 325]

More Articles...