Studies in Polypropionate Synthesis: Stereoselective Synthesis of (-)-Denticulatins A and B.

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

Source and publish data:

Tetrahedron Letters p. 801 - 804 (1992)

Update date:2022-08-11

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Authors:

Paterson, Ian

Perkins, Michael V.

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Article abstract of DOI:10.1016/S0040-4039(00)77719-7

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

Full text of DOI:10.1016/S0040-4039(00)77719-7

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