title: Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications.
abstract: 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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Juan F
authors.initials: JF
authors.lastname: Sanz-Cervera
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D000871:Anthelmintics / Q000138:chemical synthesis* / Q000378:metabolism; D007212:Indolizines / Q000138:chemical synthesis* / Q000378:metabolism; D010407:Penicillium / Q000737:chemistry / Q000378:metabolism; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000871:Anthelmintics; D007212:Indolizines; D013141:Spiro Compounds; C084043:VM 55599; C063985:paraherquamide