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

Authors
Sono, M Hashimoto, A Nakashima, K Tori, M
Citation
M. Sono et al., Total synthesis of coronafacic acid through 6-endo-trig mode intramolecular cyclization of an enone-aldehyde to a hydrindanone using samarium(II) iodide, TETRAHEDR L, 41(26), 2000, pp. 5115-5118
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
26
Year of publication
2000
Pages
5115 - 5118
Database
ISI
SICI code
0040-4039(20000624)41:26<5115:TSOCAT>2.0.ZU;2-1
Abstract
Coronafacic acid has been synthesized from a hydrindanone prepared by a 6-e ndo-trig mode cyclization reaction of the enone-aldehyde with samarium(II) iodide. The stereochemistry of the hydrindanone was controlled by the coord inated samarium species resulting in cis in respect of the hydroxyl group a t C-4 and the juncture proton at C-3a. (C) 2000 Elsevier Science Ltd. All r ights reserved.