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  • Title: Synthesis of the ABC fragment of the pectenotoxins.
    Author: Halim R, Brimble MA, Merten J.
    Journal: Org Lett; 2005 Jun 23; 7(13):2659-62. PubMed ID: 15957915.
    Abstract:
    [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.
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