A two-directional synthesis of the C58-C71 fragment of palytoxin.
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.
Hodgson
Robert
R
Department of Chemistry, University of Leeds, Leeds, UK LS2 9JT.
Nelson
Adam
A
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
D000178:Acrylamides; D003064:Cnidarian Venoms; D004952:Esters; C010272:palytoxin; D000095702:Polyether Toxins