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Total Synthesis of (−)-Steganone Utilizing a Samarium(II) Iodide Promoted 8-Endo Ketyl−Olefin Cyclization

✍ Scribed by Monovich, Lauren G.; Le Huérou, Yvan; Rönn, Magnus; Molander, Gary A.

Book ID: 119966841
Publisher: American Chemical Society
Year: 2000
Tongue: English
Weight: 236 KB
Volume: 122
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja9930059

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Coronafacic acid has been synthesized from a hydrindanone prepared by a 6-endo-trig mode cyclization reaction of the enone-aldehyde with samarium(II) iodide. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species resulting in cis in respect of the hydroxyl group a