Abstract
The enantioselective synthesis of (8R,8aS)-hcxahydro-8-methyl-5(1H)-indolizinone ((-)-13), which is a synthetic intermediate of 5,8-disubstituted indolizidine alkaloids has been carried out. Reaction of ethyl (E)-(4R, 5R)-8-benzyloxy-4, 5-epoxy-4-methyl-2-octenoate (4) with formic acid in the presence of Pd2(dba)3CHCl3 and n-Bu3P as a catalyst gave ethyl (E)-(4R, 5R)-8-benzyloxy-5-hydroxy-4-methyl-2-octenoate (5), which was converted to (-)-13 in 8 and steps.
| Original language | English |
|---|---|
| Pages (from-to) | 1405-1408 |
| Number of pages | 4 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 4 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - 1993 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
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A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone. / Satake, Akiharu; Shimizu, Isao.
In: Tetrahedron: Asymmetry, Vol. 4, No. 7, 1993, p. 1405-1408.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone
AU - Satake, Akiharu
AU - Shimizu, Isao
PY - 1993
Y1 - 1993
N2 - The enantioselective synthesis of (8R,8aS)-hcxahydro-8-methyl-5(1H)-indolizinone ((-)-13), which is a synthetic intermediate of 5,8-disubstituted indolizidine alkaloids has been carried out. Reaction of ethyl (E)-(4R, 5R)-8-benzyloxy-4, 5-epoxy-4-methyl-2-octenoate (4) with formic acid in the presence of Pd2(dba)3CHCl3 and n-Bu3P as a catalyst gave ethyl (E)-(4R, 5R)-8-benzyloxy-5-hydroxy-4-methyl-2-octenoate (5), which was converted to (-)-13 in 8 and steps.
AB - The enantioselective synthesis of (8R,8aS)-hcxahydro-8-methyl-5(1H)-indolizinone ((-)-13), which is a synthetic intermediate of 5,8-disubstituted indolizidine alkaloids has been carried out. Reaction of ethyl (E)-(4R, 5R)-8-benzyloxy-4, 5-epoxy-4-methyl-2-octenoate (4) with formic acid in the presence of Pd2(dba)3CHCl3 and n-Bu3P as a catalyst gave ethyl (E)-(4R, 5R)-8-benzyloxy-5-hydroxy-4-methyl-2-octenoate (5), which was converted to (-)-13 in 8 and steps.
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UR - http://www.scopus.com/inward/citedby.url?scp=0027292517&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(00)80326-2
DO - 10.1016/S0957-4166(00)80326-2
M3 - Article
AN - SCOPUS:0027292517
VL - 4
SP - 1405
EP - 1408
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 7
ER -