A Model Study toward the Concise Synthesis of Bromotyrosine-Derived Spiroisoxazoline Natural Products and Analogous Core Structures

Prasanta Das
Edward J. Valente, University of Portland
Ashton T. Hamme II

European Journal of Organic Chemistry, 2014, Volume 2014, Issue 13, 2659–2663.

© 2014 Wiley-VCH Verlag GmbH & Co.KGaA, Weinheim

Linked version is the final published version.

Abstract

A model study of the first nonaromatic ring based approach toward α-hydroxyspiroisoxazolines resembling the bromotyrosine-derived natural product and analogous spiroisoxazoline core structures was implemented.The desired molecular architecture was achieved through the multifunctionalization of a key 1,3-diketo spiroisoxazoline.Our strategy could serve as an efficient alternative to previously developed approaches that involve aromatic ring oxidation as the essential step to synthesize this class of natural products.