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Journal Article

Total Synthesis of Caloporoside

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Konetzki,  Ingo
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Konetzki, I. (1998). Total Synthesis of Caloporoside. The Journal of Organic Chemistry, 63(9), 3072-3080. doi:10.1021/jo9800098.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-20DD-4
Abstract
The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-d-glucopyranose 14 as a common building block, with d-gluco → d-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27 → 28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of β-d-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.