Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B.
The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.
D000470:Alkaloids / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D012492:Salts / Q000737:chemistry
D000470:Alkaloids; D000480:Alkynes; D003517:Cyclopentanes; D023303:Oxazolidinones; D012492:Salts; C464968:agelastatin A; C464967:agelastatin B