Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications.

Juan F Sanz-Cervera, Robert M Williams

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.

Journal of the American Chemical Society 2002 Mar 20

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The first asymmetric biomimetic total synthesis of VM55599 (13) has been achieved utilizing an intramolecular Diels-Alder cycloaddition as a key step. The synthetic material was utilized to elucidate the absolute stereochemistry of the natural product. The results are discussed in terms of a unified biogenesis of the paraherquamides and VM55599.

Citation

Juan F Sanz-Cervera, Robert M Williams. Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications. Journal of the American Chemical Society. 2002 Mar 20;124(11):2556-9