Abstract
The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.
| Original language | English |
|---|---|
| Pages (from-to) | 2111-2119 |
| Number of pages | 9 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2014 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 2014 |
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Keywords
- Asymmetric synthesis
- Natural products
- Olefination
- Phytoprostanes
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
Cite this
A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester. / Porta, Alessio; Chiesa, Francesco; Quaroni, Marco; Persico, Marco; Moratti, Remigio; Zanoni, Giuseppe; Vidari, Giovanni.
In: European Journal of Organic Chemistry, Vol. 2014, No. 10, 2014, p. 2111-2119.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester
AU - Porta, Alessio
AU - Chiesa, Francesco
AU - Quaroni, Marco
AU - Persico, Marco
AU - Moratti, Remigio
AU - Zanoni, Giuseppe
AU - Vidari, Giovanni
PY - 2014
Y1 - 2014
N2 - The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.
AB - The first syntheses of 9-J1-phytoprostane and 9-A 1-phytoprostane methyl ester were achieved enantioselectively using a divergent approach from a common intermediate sulfone 4. The divergence was accomplished using a sigmatropic rearrangement (swap protocol) to give sulfone 5 in 47% overall yield. The two upper side-chains, with a stereodefined E double bond, were installed using consolidated Julia-Lythgoe olefination reactions of sulfones 4 and 5, with the same enantiopure α-protected aldehyde 6.
KW - Asymmetric synthesis
KW - Natural products
KW - Olefination
KW - Phytoprostanes
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=84897112220&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84897112220&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201301703
DO - 10.1002/ejoc.201301703
M3 - Article
AN - SCOPUS:84897112220
VL - 2014
SP - 2111
EP - 2119
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 10
ER -