Studies in polypropionate synthesis: stereoselective synthesis of (-)-denticulatins A and B

Ian Paterson; Michael V. Perkins

doi:10.1016/S0040-4039(00)77719-7

Studies in polypropionate synthesis: stereoselective synthesis of (-)-denticulatins A and B

Ian Paterson, Michael V. Perkins

Research output: Contribution to journal › Article › peer-review

83 Citations (Scopus)

Abstract

()-Denticulatin B(2) was prepared in 9 steps (20% yield) with 70% overall ds starting from the ethyl ketone (R)-8. Key steps are the novel boron-mediated aldol/reduction, 8 → 12, the titanium aldol couping, 6 + 5 → 18, and the HF-pyridine cyclisation, 20 → 2. Epimerisation at C₁₀ in 20 led to ()-denticulatin A (1).

Original language	English
Pages (from-to)	801-804
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(00)77719-7
Publication status	Published - 4 Feb 1992
Externally published	Yes

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title = "Studies in polypropionate synthesis: stereoselective synthesis of (-)-denticulatins A and B",

abstract = "()-Denticulatin B(2) was prepared in 9 steps (20% yield) with 70% overall ds starting from the ethyl ketone (R)-8. Key steps are the novel boron-mediated aldol/reduction, 8 → 12, the titanium aldol couping, 6 + 5 → 18, and the HF-pyridine cyclisation, 20 → 2. Epimerisation at C10 in 20 led to ()-denticulatin A (1).",

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N2 - ()-Denticulatin B(2) was prepared in 9 steps (20% yield) with 70% overall ds starting from the ethyl ketone (R)-8. Key steps are the novel boron-mediated aldol/reduction, 8 → 12, the titanium aldol couping, 6 + 5 → 18, and the HF-pyridine cyclisation, 20 → 2. Epimerisation at C10 in 20 led to ()-denticulatin A (1).

AB - ()-Denticulatin B(2) was prepared in 9 steps (20% yield) with 70% overall ds starting from the ethyl ketone (R)-8. Key steps are the novel boron-mediated aldol/reduction, 8 → 12, the titanium aldol couping, 6 + 5 → 18, and the HF-pyridine cyclisation, 20 → 2. Epimerisation at C10 in 20 led to ()-denticulatin A (1).

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Studies in polypropionate synthesis: stereoselective synthesis of (-)-denticulatins A and B

Abstract

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