A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone

Akiharu Satake; Isao Shimizu

doi:10.1016/S0957-4166(00)80326-2

A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone

Akiharu Satake, Isao Shimizu

Waseda University

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

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	https://doi.org/10.1016/S0957-4166(00)80326-2
Publication status	Published - 1993

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Drug Discovery

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title = "A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone",

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.",

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T1 - A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone

AU - Satake, Akiharu

AU - Shimizu, Isao

PY - 1993

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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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