Total Synthesis of (−)-Mucosin and Revision of Structure
2018
Nolsøe, Jens M. J. | Antonsen, Simen | Görbitz, Carl H. | Hansen, Trond V. | Nesman, Jannicke I. | Røhr, Åsmund K. | Stenstrøm, Yngve H.
The first total synthesis of (−)-mucosin (6), an unusual marine hydrindane natural product incorporating a prostaglandin-like submotif, has been achieved. As a result of the campaign, three of the four all-carbon stereocenters in the purported structure 1 have been revised. Of particular note is the excellent control over β-chirality in conjugate addition to ester (−)-22 and the facial selectivity in the subsequent protonation of an intermediate silyl ketene acetal.
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