Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

• Mikko Passiniemi and
• Ari M.P. Koskinen

Beilstein J. Org. Chem. 2013, 9, 2641–2659, doi:10.3762/bjoc.9.300

• )-vinyl nucleophiles created from the vinyl iodide 61 in the stereoselective synthesis of pachastrissamine (11) [81][82] and norfuranomycin [37] (Scheme 23). After halogen–metal exchange with n-BuLi, the newly formed nucleophile reacts with (S)-1. When HMPT or dimethylpropyleneurea (DMPU) were used, high

• of Garner’s aldehyde. Structures of some iminosugars (7, 9), peptide antibiotics (8) and sphingosine (10) and pachastrissamine (11). (a) i) Boc2O, 1.0 N NaOH (pH >10), dioxane, +5 °C → rt; ii) MeI, K2CO3, DMF, 0 °C → rt (86% over two steps); (b) Me2C(OMe)2, cat. p-TsOH, benzene, reflux (70–89%); (c

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

• Volker M. Schmiedel,
• Stefano Stefani and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2013, 9, 2564–2569, doi:10.3762/bjoc.9.291

• . Keywords: chiral auxiliaries; gold catalysis; jaspine B; lithiated alkoxyallenes; natural product synthesis; pachastrissamine; tetrahydrofurans; Introduction Jaspine B, also known as pachastrissamine (1, Scheme 1), is an anhydrophytosphingosine derivative, isolated 2002 from the marine sponge Pachastrissa