Abstract
The Lewis acid mediated reaction of α-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).
| Original language | English |
|---|---|
| Pages (from-to) | 3562-3566 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 124 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - Apr 10 2002 |
| Externally published | Yes |
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Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis. / Kadota, Isao; Ohno, Akio; Matsuda, Kumiko; Yamamoto, Yoshinori.
In: Journal of the American Chemical Society, Vol. 124, No. 14, 10.04.2002, p. 3562-3566.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis
AU - Kadota, Isao
AU - Ohno, Akio
AU - Matsuda, Kumiko
AU - Yamamoto, Yoshinori
PY - 2002/4/10
Y1 - 2002/4/10
N2 - The Lewis acid mediated reaction of α-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).
AB - The Lewis acid mediated reaction of α-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).
UR - http://www.scopus.com/inward/record.url?scp=0037051647&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037051647&partnerID=8YFLogxK
U2 - 10.1021/ja025523g
DO - 10.1021/ja025523g
M3 - Article
C2 - 11929244
AN - SCOPUS:0037051647
VL - 124
SP - 3562
EP - 3566
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 14
ER -