Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide

Gamal A I Moustafa; Yasumasa Kamada; Tetsuaki Tanaka; Takehiko Yoshimitsu

doi:10.1039/c2ob26532j

Stereoconvergent route to chiral cyclohexenone building blocks

Formal synthesis of (-)-dysidiolide

Gamal A I Moustafa, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.

Original language	English
Pages (from-to)	8609-8615
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	43
DOIs	https://doi.org/10.1039/c2ob26532j
Publication status	Published - Nov 21 2012
Externally published	Yes

Fingerprint

Stereoisomerism

activity (biology)

routes

synthesis

dysidiolide

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

Cite this

Moustafa, G. A. I., Kamada, Y., Tanaka, T., & Yoshimitsu, T. (2012). Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide. Organic and Biomolecular Chemistry, 10(43), 8609-8615. https://doi.org/10.1039/c2ob26532j

Stereoconvergent route to chiral cyclohexenone building blocks : Formal synthesis of (-)-dysidiolide. / Moustafa, Gamal A I; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 43, 21.11.2012, p. 8609-8615.

Research output: Contribution to journal › Article

Moustafa, GAI, Kamada, Y, Tanaka, T & Yoshimitsu, T 2012, 'Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide', Organic and Biomolecular Chemistry, vol. 10, no. 43, pp. 8609-8615. https://doi.org/10.1039/c2ob26532j

Moustafa GAI, Kamada Y, Tanaka T, Yoshimitsu T. Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide. Organic and Biomolecular Chemistry. 2012 Nov 21;10(43):8609-8615. https://doi.org/10.1039/c2ob26532j

Moustafa, Gamal A I ; Kamada, Yasumasa ; Tanaka, Tetsuaki ; Yoshimitsu, Takehiko. / Stereoconvergent route to chiral cyclohexenone building blocks : Formal synthesis of (-)-dysidiolide. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 43. pp. 8609-8615.

@article{c841e7611f4345dab43e43bbf1a1c425,

title = "Stereoconvergent route to chiral cyclohexenone building blocks: Formal synthesis of (-)-dysidiolide",

abstract = "A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.",

author = "Moustafa, {Gamal A I} and Yasumasa Kamada and Tetsuaki Tanaka and Takehiko Yoshimitsu",

year = "2012",

month = "11",

day = "21",

doi = "10.1039/c2ob26532j",

language = "English",

volume = "10",

pages = "8609--8615",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "43",

}

TY - JOUR

T1 - Stereoconvergent route to chiral cyclohexenone building blocks

T2 - Formal synthesis of (-)-dysidiolide

AU - Moustafa, Gamal A I

AU - Kamada, Yasumasa

AU - Tanaka, Tetsuaki

AU - Yoshimitsu, Takehiko

PY - 2012/11/21

Y1 - 2012/11/21

N2 - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.

AB - A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3′-Hydroxy-4′-methylpent-4′-enyl)-3-methoxy cyclohex-2-enone (1) that consists of four stereoisomers, i.e., racemic ca. 1:1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.

UR - http://www.scopus.com/inward/record.url?scp=84867514330&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84867514330&partnerID=8YFLogxK

U2 - 10.1039/c2ob26532j

DO - 10.1039/c2ob26532j

M3 - Article

VL - 10

SP - 8609

EP - 8615

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 43

ER -

Access to Document

10.1039/c2ob26532j