The Total Synthesis of Eleutherobin
Journal of the American Chemical Society1999Vol. 121(28), pp. 6563–6579
Citations Over TimeTop 10% of 1999 papers
Xiaotao Chen, Samit K. Bhattacharya, Bishan Zhou, Clare E. Gutteridge, Thomas R. R. Pettus, Samuel J. Danishefsky
Abstract
The total synthesis of the title compound (1), starting with (R)-(−)-α-phellandrene (6), has been accomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid and carbohydrate domains of eleutherobin. Key reactions included a Nozaki−Kishi ring closure to produce a furanophane (see 37 → 38), a pyranose to furanose transposition (see 50 → 47), and a novel oxycarbaglycosidation (cf. 58 → 87) for joining the two domains.
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