A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.
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.
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA 92697-2025 (USA) http://www.chem.uci.edu/∼cdv.
Won-Jin
WJ
Chung
Joseph S
JS
Carlson
D Karl
DK
Bedke
Christopher D
CD
Vanderwal
D001688:Biological Products; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D013451:Sulfonic Acids; C000590665:mytilipin A; C015518:sulfolipids; C013880:chlorosulfonic acid
kinetic resolution; lipids; metathesis; natural products; total synthesis