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Total synthesis of coronafacic acid through 6-endo-trig mode intramolecular cyclization of an enone-aldehyde to a hydrindanone using samarium(II) iodide

✍ Scribed by Masakazu Sono; Atsuko Hashimoto; Katsuyuki Nakashima; Motoo Tori


Book ID
104210479
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
124 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


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 at C-4 and the juncture proton at C-3a.