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

• Volker M. Schmiedel Stefano Stefani Hans-Ulrich Reissig Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany 10.3762/bjoc.9.291 Abstract Herein we present the synthesis of the anhydrophytosphingosine jaspine B and three of its stereoisomers using a

• . 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

• sp. by Higa et al. [1]. In 2003 Debitus et al. were able to extract this natural product from the marine sponge Jaspis sp. [2]. Jaspine B (1) comprises a densely functionalized tetrahydrofuran ring, bearing three contiguous (2S,3S,4S)-configured stereogenic centers with a long alkyl chain at C-2 and