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The Total Synthesis of Eleutherobin

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journal contribution
posted on 30.06.1999 by Xiao-Tao Chen, Samit K. Bhattacharya, Bishan Zhou, Clare E. Gutteridge, Thomas R. R. Pettus, Samuel J. Danishefsky
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 3738), a pyranose to furanose transposition (see 5047), and a novel oxycarbaglycosidation (cf. 5887) for joining the two domains.