Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2, 5-dione in carbonyl ylide cycloadditions

…, F Le Strat, TD Avery, AC Donohue…

Index: Hodgson, David M.; Le Strat, Frederic; Avery, Thomas D.; Donohue, Andrew C.; Brueckl, Tobias Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8796 - 8803

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Citation Number: 42

Abstract

Levulinic acid-derived 6-diazoheptane-2, 5-dione (9) serves as a common precursor in a formal synthesis of frontalin 19, and in syntheses of cis-nemorensic acid 1, 4-hydroxy-cis- nemorensic acid 2, 3-hydroxy-cis-nemorensic acid 3, and nemorensic acid 4. The key step in these syntheses is the Rh2 (OAc) 4-catalyzed tandem carbonyl ylide formation- intermolecular 1, 3-dipolar cycloadditions of diazodione 9 with formaldehyde, alkynes or ...

~80%

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