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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Highly polar spiroisoxazolines from the sponge Aplysina fulva
Evan W Rogers1, Tadeusz F Molinski
1Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
Abstract:
Two new highly polar brominated spiroisoxazolines, araplysillin N9-sulfamate (1) and an N-[5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxy]-4-aminobutanoic acid (2), were isolated from a sample of Aplysina fulva collected in the Florida Keys. The absolute stereostructures of the new compounds were determined from analysis of MS, 1H and 13C NMR, and CD spectroscopy. Compound 2 provides a structural clue that may unify the biosynthesis of brominated spiroisoxazolines.
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