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Molecules 2007, 12(9), 2215-2222; doi:10.3390/12092215
Article

Diastereoselective Spiroannulation of Phenolic Substrates: Advances Towards the Asymmetric Formation of the Manumycin m-C7N Core Skeleton

* , ,  and
University of Northern British Columbia, Department of Chemistry, 3333 University Way, Prince George, British Columbia, Canada
* Author to whom correspondence should be addressed.
Received: 7 September 2007 / Revised: 24 September 2007 / Accepted: 24 September 2007 / Published: 25 September 2007
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Abstract

The asymmetric syntheses of two new spirolactones prepared in optically pure form from L-3-nitrotyrosine are described. The key step, an oxidative spiroannulation, was carried out on the optically active phenols 11a and 11b and afforded the new spirolactones 5a and 5b in 85% and 83% yields, respectively, as mixtures (3:1 dr) of diastereomers. The major diastereomers from these mixtures could be isolated in optically pure form by trituration using acetone-hexanes as the solvent. Thus, the optically active spirolactones (+)-5a (+ 92.8o, c=0.125 acetone) and (+)-5b (+112.0o, c= 0.125 acetone) were obtained after four synthetic steps from L-3-nitrotyrosine in 41% and 43% yield, respectively.
Keywords: Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Manumycins; Aranorosins; Gymnastatins. Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Spiroannulation; oxidation; phenol; diastereoselective; asymmetric; Manumycins; Aranorosins; Gymnastatins.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Plourde, G.L.; Spaetzel, R.R.; Kwasnitza, J.S.; Scully, T.W. Diastereoselective Spiroannulation of Phenolic Substrates: Advances Towards the Asymmetric Formation of the Manumycin m-C7N Core Skeleton. Molecules 2007, 12, 2215-2222.

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