An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

Arun Sharma; Shantu Amin; Subodh Kumar

doi:10.1080/10406630290026920

An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

Arun Sharma
, Shantu Amin
, Subodh Kumar

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

11 Scopus citations

Abstract

Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

Original language	English (US)
Pages (from-to)	277-288
Number of pages	12
Journal	Polycyclic Aromatic Compounds
Volume	22
Issue number	3-4
DOIs	https://doi.org/10.1080/10406630290026920
State	Published - 2002

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1080/10406630290026920

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title = "An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction",

abstract = "Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.",

author = "Arun Sharma and Shantu Amin and Subodh Kumar",

note = "Funding Information: This study was supported by NCI Contract NCI-CB-77022-75 and Cancer Center Support Grant CA-17613. We thank Ms. Ilse Hoffmann for editing this manuscript. Address correspondence to Arun K. Sharma, Organic Synthesis Facility, American Health Foundation, 1 Dana Road, Valhalla, NY 10595, USA.",

year = "2002",

doi = "10.1080/10406630290026920",

language = "English (US)",

volume = "22",

pages = "277--288",

journal = "Polycyclic Aromatic Compounds",

issn = "1040-6638",

publisher = "Taylor and Francis Ltd.",

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TY - JOUR

T1 - An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

AU - Sharma, Arun

AU - Amin, Shantu

AU - Kumar, Subodh

N1 - Funding Information: This study was supported by NCI Contract NCI-CB-77022-75 and Cancer Center Support Grant CA-17613. We thank Ms. Ilse Hoffmann for editing this manuscript. Address correspondence to Arun K. Sharma, Organic Synthesis Facility, American Health Foundation, 1 Dana Road, Valhalla, NY 10595, USA.

PY - 2002

Y1 - 2002

N2 - Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

AB - Efficient syntheses of important metabolites of 7,12-dimethylbenz[a]anthracene (DMBA) and benzo[c]chrysene (B[c]C), via Suzuki coupling reaction are described. This approach provides an excellent method for the preparation of 3-methoxy-DMBA 5, 10-methoxy-B[c]C 14 and 2-methoxy B[c]C 20, and hence for the corresponding dihydrodiols 6, 15, and 21. Following a similar Suzuki reaction, DMBA-6(5 H)-one 8 was also synthesized in high yield.

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UR - https://www.scopus.com/pages/publications/0036401214#tab=citedBy

U2 - 10.1080/10406630290026920

DO - 10.1080/10406630290026920

M3 - Article

AN - SCOPUS:0036401214

SN - 1040-6638

VL - 22

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JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

IS - 3-4

ER -

An abbreviated synthesis of 7,12-dimethylbenz[a]anthracene and benzo[c]chrysene metabolites using the Suzuki reaction

Abstract

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