Abstract
Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).
| Original language | English |
|---|---|
| Pages (from-to) | 423-432 |
| Number of pages | 10 |
| Journal | Accounts of Chemical Research |
| Volume | 38 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - May 2005 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Synthetic strategies of marine polycyclic ethers via intramolecular allylations : Linear and convergent approaches. / Kadota, Isao; Yamamoto, Yoshinori.
In: Accounts of Chemical Research, Vol. 38, No. 5, 05.2005, p. 423-432.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic strategies of marine polycyclic ethers via intramolecular allylations
T2 - Linear and convergent approaches
AU - Kadota, Isao
AU - Yamamoto, Yoshinori
PY - 2005/5
Y1 - 2005/5
N2 - Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).
AB - Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).
UR - http://www.scopus.com/inward/record.url?scp=20444454650&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=20444454650&partnerID=8YFLogxK
U2 - 10.1021/ar040118a
DO - 10.1021/ar040118a
M3 - Article
VL - 38
SP - 423
EP - 432
JO - Accounts of Chemical Research
JF - Accounts of Chemical Research
SN - 0001-4842
IS - 5
ER -