title: A convergent route to the CDEF-tetracycle of pectenotoxin-2.
abstract: A convergent synthesis of the CDEF-tetracyclic region of pectenotoxin-2 (PTX-2) is described. The synthetic pathway derives from a head-to-tail union of 2 equiv of linalool to establish a stereodefined DEF-tricyclic aldehyde. Subsequent coupling with a "northern" fragment enolate, followed by a tandem Sharpless epoxidation/cyclization, delivers the C10-C26 polycyclic region of the natural product.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, United States.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Canterbury
authors.forename: Glenn C
authors.initials: GC
authors.lastname: Micalizio
mesh_terms: D005663:Furans / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D018942:Macrolides; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D018942:Macrolides; D011714:Pyrans; C098380:pectenotoxin 2; D000095702:Polyether Toxins