Abstract
A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.
| Original language | English |
|---|---|
| Pages (from-to) | 4492-4495 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 59 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - Dec 19 2018 |
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Keywords
- Allylation
- Convergent synthesis
- Enigmazole A
- Macrolide
- Reductive acetylation
- Total synthesis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Formal total synthesis of enigmazole A. / Meissner, Andreas; Kishi, Takayuki; Fujisawa, Yuka; Murai, Yuto; Takamura, Hiroyoshi; Kadota, Isao.
In: Tetrahedron Letters, Vol. 59, No. 51, 19.12.2018, p. 4492-4495.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Formal total synthesis of enigmazole A
AU - Meissner, Andreas
AU - Kishi, Takayuki
AU - Fujisawa, Yuka
AU - Murai, Yuto
AU - Takamura, Hiroyoshi
AU - Kadota, Isao
PY - 2018/12/19
Y1 - 2018/12/19
N2 - A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.
AB - A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.
KW - Allylation
KW - Convergent synthesis
KW - Enigmazole A
KW - Macrolide
KW - Reductive acetylation
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=85056659428&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85056659428&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2018.11.017
DO - 10.1016/j.tetlet.2018.11.017
M3 - Article
AN - SCOPUS:85056659428
VL - 59
SP - 4492
EP - 4495
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 51
ER -