title: A two-directional synthesis of the C58-C71 fragment of palytoxin.
abstract: A two directional approach, in which asymmetric dihydroxylation and reduction reactions were used to control absolute configuration, was exploited in the preparation of a C(2)-symmetrical dipyranone. The homotopic dihydropyran (DHP) rings of this precursor were differentiated statistically using by a Prevost reaction and further functionalisation. A second Prevost reaction was used to functionalise the other DHP; global deprotection and peracetylation gave a protected version of the C(58)-C(71) fragment of palytoxin. Methods which might be of value in future synthetic work were developed for the stereoselective functionalisation of THP rings similar to those found in this fragment.
authors.affiliation: Department of Chemistry, University of Leeds, Leeds, UK LS2 9JT.
authors.forename: Robert
authors.initials: R
authors.lastname: Hodgson
authors.forename: Adam
authors.initials: A
authors.lastname: Nelson
mesh_terms: D000107:Acetylation; D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D003064:Cnidarian Venoms; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000178:Acrylamides; D003064:Cnidarian Venoms; D004952:Esters; C010272:palytoxin; D000095702:Polyether Toxins