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A Synthesis of the Chlorosulfolipid Mytilipin A via a Longest Linear Sequence of Seven Steps

2013; Wiley; Volume: 52; Issue: 38 Linguagem: Inglês

10.1002/anie.201304565

1521-3773

Won‐jin Chung, Joseph S. Carlson, D. Karl Bedke, Christopher D. Vanderwal,

Carbohydrate Chemistry and Synthesis

Magnificent seven: The chlorosulfolipid mytilipin A was synthesized in racemic form in seven steps and in enantioenriched form in eight steps. Key transformations include a highly diastereoselective bromoallylation of a sensitive α,β-dichloroaldehyde, a kinetic resolution of a vinyl epoxide, a convergent and highly Z-selective alkene cross-metathesis, and a chemoselective and diastereoselective dichlorination of a complex diene.