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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Dinoflagellida / chemistry
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Epoxy Compounds / chemistry
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Fructose / chemistry
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Macrolides
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Marine Toxins / chemical synthesis*
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Molecular Structure
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Peptide Fragments / chemical synthesis*
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Pyrans / chemical synthesis*
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Pyrans / chemistry*
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry*
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Stereoisomerism
Substances
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Epoxy Compounds
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Macrolides
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Marine Toxins
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Peptide Fragments
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Pyrans
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Spiro Compounds
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pectenotoxin 7
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dioxirane
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Fructose