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Beilstein J. Org. Chem. 2013, 9, 2564–2569, doi:10.3762/bjoc.9.291
Graphical Abstract
Scheme 1: Structure of jaspine B 1 and its stereoisomers 2–4.
Scheme 2: Retrosynthetic analysis of jaspine B leading to pentadecanal and an alkoxyallene.
Scheme 3: Synthesis of racemic dihydrofuran 8.
Scheme 4: Synthesis of racemic jaspine B rac-1 and its diastereomer rac-2.
Scheme 5: Synthesis of dihydrofurans 14 and 15.
Scheme 6: Synthesis of jaspine B (1) and its (2S,3R,4R)-diastereomer 2.
Scheme 7: Protection and separation of the diastereomers.
Scheme 8: Reduction of the separated diastereomers leading to jaspine B (1) and its diastereomer 2.
Scheme 9: Route to ent-jaspine B (3) and the (2R,3S,4S)-diastereomer 4.