Synthesis of the ABC fragment of the pectenotoxins.
[reaction: see text] A highly stereocontrolled synthesis of the C1-C16 ABC spiroacetal-containing fragment 5 of PTX7 (4) has been achieved. Appendage of the C ring to the AB fragment involved Wittig reaction of spiroacetal aldehyde 8 with a stabilized ylide 9 followed by displacement of allylic iodide 27 with a lithium acetylide to afford enyne 7. Fructose-derived chiral dioxirane and dihydroxylation were then used to introduce the correct functionality in the tetrahydrofuran C ring.
Halim
Rosliana
R
Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Brimble
Margaret A
MA
Merten
Jörn
J
D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D018942:Macrolides; D008387:Marine Toxins / Q000138:chemical synthesis*; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D004852:Epoxy Compounds; D005632:Fructose; D018942:Macrolides; D008387:Marine Toxins; D010446:Peptide Fragments; D011714:Pyrans; D013141:Spiro Compounds; C508863:pectenotoxin 7; D000095702:Polyether Toxins; C061799:dioxirane