The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.027) dodecan-5-one

A. Fisher; E. Oppenheimer; S. Cohen

doi:10.1016/0040-4020(75)80040-8

The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.0²⁷) dodecan-5-one

A. Fisher^*, E. Oppenheimer, S. Cohen

^*Corresponding author for this work

Physiology Pharmacology

Tel Aviv University

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

6 Scopus citations

Abstract

Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH₄ reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.0^2,7)dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-(trans-3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone.

Original language	English
Pages (from-to)	317-325
Number of pages	9
Journal	Tetrahedron
Volume	31
Issue number	4
DOIs	https://doi.org/10.1016/0040-4020(75)80040-8
State	Published - 1975

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title = "The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.027) dodecan-5-one",

abstract = "Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH4 reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.02,7)dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-(trans-3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone.",

author = "A. Fisher and E. Oppenheimer and S. Cohen",

year = "1975",

doi = "10.1016/0040-4020(75)80040-8",

language = "אנגלית",

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pages = "317--325",

journal = "Tetrahedron",

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T1 - The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.027) dodecan-5-one

AU - Fisher, A.

AU - Oppenheimer, E.

AU - Cohen, S.

PY - 1975

Y1 - 1975

N2 - Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH4 reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.02,7)dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-(trans-3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone.

AB - Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH4 reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.02,7)dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-(trans-3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone.

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The fused quinuclidine-valerolactone system Synthesis and conformation of 4-alkyl or 4-aryl-6-oxa-1-azatricyclo (4.2.2.0²⁷) dodecan-5-one

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