Spiculoic acid

Tadano K-i (2009) Natural product synthesis featuring intramolecular Diels-Alder approaches - Total Syntheses of tubelactomicins and spiculoic acid A. Eur J Oig Chem 4381 394... 

A model system for the marine sponge metabolite, spiculoic acid 147 was generated by an intramolecular Diels-Alder reaction. The requisite triene 146 was prepared using a Wittig reaction. To this end, aldehyde 144 was coupled with ylide 145. The resultant 146 was not isolated and underwent an intramoleeular Diels-Alder reaction to generate a mixture of adducts, 148 and 149. 

Kirkham, J.E.D., Lee, V., and Baldwin, J.E. (2006) Biomimetic synthesis of marine sponge metabolite spiculoic acid A and establishment of the absolute configuration of the natural product Chem. Commun., 2863-2865. 

Roche ester, (R)-3-hydroxy-2-methylpropionic acid methyl ester (16b), is a chiral building block for the synthesis of vitamins (a-tocopherol), natural products (spiculoic acid A), antibiotics (calcimycin), and fragrance components (muscone) and therefore of high interest for industry. Faber and coworkers employed ERs for the asymmetric synthesis of methyl 2-hydroxymethylacrylate derivatives... 

Berrue, F., Thomas, O.P., Fernandez, R., and Amade, P. (2005a) Iso, nor-, and dinor-spiculoic acids A, polyketides from the marine sponge Plakortiszyggompha. J. Nat. Prod., 68, 547-549. 

Huang, X.-H., Van Soest, R Roberge, M and Andersen, R.J. (2004) Spiculoic acids A and B, new polyketides isolated from the Caribbean marine sponge Plakortis angulospiculatus, Org, Lett, 6, 75-78. 

Mehta, G. and Kundu, U.K. (2005) Toward a total synthesis of the novel polyketide natural product spiculoic acid A. Otg. Lett., 7, 5569-5572. 

Several new acids related to spiculoic add A were found subsequently in the species Plakortis zyggompha harvested in Martinique. These contain all the original skeleton of trans-hydrindan-2-one and a detailed structural study has revealed the definitive stereochemistry of all compounds of this family (Berrue et al, 2005a, 2007). AH of these polyketide-type derivatives are moderately cytotoxic or antimycobacterial. 

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