Abstract
We have developed a systematic synthesis of the poly-THF ring cores of anti-tumor Annonaceous acetogenins by utilizing asymmetric alkynylation and subsequent stereodivergent THF ring formation as key steps. The asymmetric alkynylation of α-oxyaldehyde and α-tetrahydrofuranic aldehyde with an (S)-3-butyne-1,2-diol derivative proceeded in good yield with very high diastereoselectivity. These adducts were converted into mono- and bis-THF cores by two different methods involving one-pot THF ring formation. The total syntheses of murisolin, 16,19-cis-murisolin, and longimicin D, which show cytotoxic activity against the human tumor cell, were accomplished by applying this methodology.
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1 Introduction
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2 Synthetic Strategy
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3 Asymmetric Alkynylation of α-Oxyaldehyde with a C4-Unit
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4 Systematic Synthesis of Mono-THF Segments by Stereodivergent THF Ring Formation
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5 Systematic Synthesis of Bis-THF Segments by an Iterative Process
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6 Total Synthesis of Murisolins and Longimicin D
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7 Conclusion
Key words
total synthesis - natural products - asymmetric synthesis - diastereoselectivity
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