Practical synthesis of (-)-morphine

Johann Mulzer; Dirk Trauner

doi:10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G

Practical synthesis of (-)-morphine

Johann Mulzer, Dirk Trauner

Chemistry

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

Abstract

The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (-)-dihydrocodeinone (16) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen-step synthesis are the conjugate addition of vinyl cuprate to 6, which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9.

Original language	English (US)
Pages (from-to)	475-482
Number of pages	8
Journal	Chirality
Volume	11
Issue number	5-6
DOIs	https://doi.org/10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G
State	Published - 1999

Keywords

Asymmetric synthesis of morphinane derivatives
Chiral resolution by column chromatography
Conjugate cuprate addition

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G

Cite this

@article{f7835c0b2a0a43bd8acc7db9b383045e,

title = "Practical synthesis of (-)-morphine",

abstract = "The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (-)-dihydrocodeinone (16) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen-step synthesis are the conjugate addition of vinyl cuprate to 6, which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9.",

keywords = "Asymmetric synthesis of morphinane derivatives, Chiral resolution by column chromatography, Conjugate cuprate addition",

author = "Johann Mulzer and Dirk Trauner",

year = "1999",

doi = "10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G",

language = "English (US)",

volume = "11",

pages = "475--482",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "5-6",

}

TY - JOUR

T1 - Practical synthesis of (-)-morphine

AU - Mulzer, Johann

AU - Trauner, Dirk

PY - 1999

Y1 - 1999

N2 - The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (-)-dihydrocodeinone (16) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen-step synthesis are the conjugate addition of vinyl cuprate to 6, which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9.

AB - The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (-)-dihydrocodeinone (16) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen-step synthesis are the conjugate addition of vinyl cuprate to 6, which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9.

KW - Asymmetric synthesis of morphinane derivatives

KW - Chiral resolution by column chromatography

KW - Conjugate cuprate addition

UR - http://www.scopus.com/inward/record.url?scp=0033065781&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033065781&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G

DO - 10.1002/(SICI)1520-636X(1999)11:5/6<475::AID-CHIR20>3.0.CO;2-G

M3 - Article

AN - SCOPUS:0033065781

VL - 11

SP - 475

EP - 482

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 5-6

ER -

Practical synthesis of (-)-morphine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this