PMID: 11929244Apr 4, 2002Paper

Convergent synthesis of polycyclic ethers via the intramolecular allylation of alpha-acetoxy ethers and subsequent ring-closing metathesis

Journal of the American Chemical Society
Isao KadotaYoshinori Yamamoto

Abstract

The Lewis acid mediated reaction of alpha-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

Citations

Jul 11, 2003·Bioorganic & Medicinal Chemistry Letters·Haruhiko FuwaMakoto Sasaki
Jan 20, 2009·The Journal of Organic Chemistry·K C Nicolaou
Nov 12, 2009·Angewandte Chemie·Anne BoussonnièreJacques Lebreton
Jul 1, 2010·Natural Product Reports·Minoru Isobe, Akinari Hamajima
Jan 5, 2019·The Journal of Antibiotics·Noah A Setterholm, Frank E McDonald
Sep 4, 2008·Angewandte Chemie·K C NicolaouRobert J Aversa
Jun 29, 2011·Israel Journal of Chemistry·K C Nicolaou, Robert J Aversa
May 16, 2009·Organic Letters·Hiroyoshi TakamuraYoshinori Yamamoto
Jun 21, 2007·The Journal of Organic Chemistry·Yoshinori Yamamoto
Sep 25, 2003·Journal of the American Chemical Society·Isao KadotaYoshinori Yamamoto
Aug 27, 2005·Organic Letters·Hiroki FurutaYuji Mori
May 18, 2005·Accounts of Chemical Research·Isao Kadota, Yoshinori Yamamoto
Aug 3, 2011·Organic Letters·Hiroyoshi TakamuraIsao Kadota
Jan 8, 2003·Journal of the American Chemical Society·Isao KadotaYoshinori Yamamoto
Aug 17, 2002·Organic Letters·Haruhiko FuwaKazuo Tachibana
Dec 12, 2002·Journal of the American Chemical Society·Haruhiko FuwaMakoto Sasaki
Mar 14, 2003·Organic Letters·Utpal MajumderJon D Rainier
Dec 15, 2005·Chemical Reviews·Tadashi Nakata
Dec 15, 2005·Chemical Reviews·Masayuki Inoue
Jun 23, 2005·Journal of the American Chemical Society·Isao KadotaYoshinori Yamamoto
May 13, 2004·Chemical Reviews·Itaru Nakamura, Yoshinori Yamamoto
May 13, 2004·Chemical Reviews·Alexander Deiters, Stephen F Martin

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