Synthesis of the ABC fragment of the pectenotoxins |
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Authors: | Halim Rosliana Brimble Margaret A Merten Jörn |
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Affiliation: | Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand. |
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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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