Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

Charles Fehr; José Galindo; Iris Farris; Ana Cuenca

doi:10.1002/hlca.200490157

Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

Charles Fehr^*
, José Galindo
, Iris Farris
, Ana Cuenca

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

30 Citations (Scopus)

Abstract

A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C₁₅ macrocyclic system is obtained by ozonolysis (Scheme 7).

Original language	English
Pages (from-to)	1737-1747
Number of pages	11
Journal	Helvetica Chimica Acta
Volume	87
Issue number	7
DOIs	https://doi.org/10.1002/hlca.200490157
Publication status	Published - 2004
Externally published	Yes

Keywords

Conjugate addition
Asymmetric protonation
Olefin synthesis
Acyclic enones
Hydrogenation
(r)-muscone
Fragmentaation
Derivatives
(s)-muscone
Ligand

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10.1002/hlca.200490157

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abstract = "A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C15 macrocyclic system is obtained by ozonolysis (Scheme 7).",

keywords = "Conjugate addition, Asymmetric protonation, Olefin synthesis, Acyclic enones, Hydrogenation, (r)-muscone, Fragmentaation, Derivatives, (s)-muscone, Ligand",

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T1 - Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

AU - Fehr, Charles

AU - Galindo, José

AU - Farris, Iris

AU - Cuenca, Ana

PY - 2004

Y1 - 2004

N2 - A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C15 macrocyclic system is obtained by ozonolysis (Scheme 7).

AB - A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C15 macrocyclic system is obtained by ozonolysis (Scheme 7).

KW - Conjugate addition

KW - Asymmetric protonation

KW - Olefin synthesis

KW - Acyclic enones

KW - Hydrogenation

KW - (r)-muscone

KW - Fragmentaation

KW - Derivatives

KW - (s)-muscone

KW - Ligand

UR - https://www.scopus.com/pages/publications/4043131581

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000223221900011&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1002/hlca.200490157

DO - 10.1002/hlca.200490157

M3 - Article

AN - SCOPUS:4043131581

SN - 0018-019X

VL - 87

SP - 1737

EP - 1747

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 7

ER -

Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

Abstract

Keywords

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