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DOI: 10.1021/JO951854I

Stereoselective Synthesis Of New Chlorophyll A Related Antioxidants Isolated From Marine Organisms

Lifu Ma, D. Dolphin
Published 1996 · Chemistry

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A new class of natural antioxidants, chlorophyll a related chlorins 3, 4(S), 4(R), 5(R), 6, 7, 8, and 9, have been synthesized from a chlorophyll a degradation product, pheophorbide a methyl ester (1). Claisen-type intramolecular condensation of pyropheophorbide a methyl ester (2) afforded the common intermediate enol 3. Chlorin 1 and enol 3 have a propensity to undergo exocyclic ring opening by ionic bases. The organic base DBU was found to be an efficient reagent for promoting the asymmetric hydroxylation of these chlorins, using N-sulfonyloxaziridines, without cleavage of the exocyclic rings. Model studies for hydroxylactonization have shown that periodate oxidation of hydroxy ketone 10 stereoselectively and predominantly forms hydroxy lactone 17(S). Periodate oxidation of α-hydroxy 1,3-diketone 4(R) and/or 4(S) to furnish hydroxy lactone 5(R) and diketone 7 was found out to be regioselective, and the site of reaction depends on the appropriate choice of reaction media. 1H NMR spectra have provided inf...



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