cis-Dihydrodiol, arene oxide and phenol metabolites of dictamnine: key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids

DR Boyd, ND Sharma, CR O'Dowd, JG Carroll…

Index: Boyd, Derek R.; Sharma, Narain D.; O'Dowd, Colin R.; Carroll, Jonathan G.; Loke, Pui L.; Allen, Christopher C. R. Chemical Communications, 2005 , # 31 p. 3989 - 3991

Full Text: HTML

Citation Number: 14

Abstract

Biotransformation of the parent furoquinoline alkaloid dictamnine and its 4- chlorofuroquinoline precursor, using the B8/36 bacterial mutant strain of Sphingomonas yanoikuyae, yielded, via biphenyl dioxygenase-catalysed dihydroxylation, the first isolable alkaloid cis-dihydrodiol metabolites; these metabolites were used in the chemoenzymatic synthesis of postulated arene oxide and phenol intermediates, and a range of derived ...

 Related Synthetic Route
Haplopine Structure

5876-17-5

Haplopine

1-Chloro-3-methyl-2-butene Structure

503-60-6

1-Chloro-3-meth...

~87%

7-Prenyloxy-gamma-Fagarine Structure

23417-92-7

7-Prenyloxy-gam...

(7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-14-4

(7S,8R)-4-metho...

~%

7-Prenyloxy-gamma-Fagarine Structure

23417-92-7

7-Prenyloxy-gam...

4-chloro-7,8-dimethoxyfuro[2,3-b]quinoline Structure

865878-27-9

4-chloro-7,8-di...

~%

7-Prenyloxy-gamma-Fagarine Structure

23417-92-7

7-Prenyloxy-gam...

Skimmianin Structure

83-95-4

Skimmianin

~%

7-Prenyloxy-gamma-Fagarine Structure

23417-92-7

7-Prenyloxy-gam...

4-methoxyfuro[2,3-b]quinoline-7,8-diol Structure

119188-51-1

4-methoxyfuro[2...

~%

7-Prenyloxy-gamma-Fagarine Structure

23417-92-7

7-Prenyloxy-gam...

(7S,8R)-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-22-4

(7S,8R)-4-metho...

~%

Robustine Structure

2255-50-7

Robustine

diazomethane Structure

186581-53-3

diazomethane

4-methoxyfuro[2,3-b]quinoline-7,8-diol Structure

119188-51-1

4-methoxyfuro[2...

~95%

Skimmianin Structure

83-95-4

Skimmianin

4-chloro-7,8-dimethoxyfuro[2,3-b]quinoline Structure

865878-27-9

4-chloro-7,8-di...

Sodium Methylate Structure

124-41-4

Sodium Methylate

~20%

Skimmianin Structure

83-95-4

Skimmianin

Skimmianin Structure

83-95-4

Skimmianin

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

4-methoxyfuro[2,3-b]quinoline-7,8-diol Structure

119188-51-1

4-methoxyfuro[2...

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

(7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-14-4

(7S,8R)-4-metho...

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

4-chloro-7,8-dimethoxyfuro[2,3-b]quinoline Structure

865878-27-9

4-chloro-7,8-di...

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

Haplopine Structure

5876-17-5

Haplopine

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

diazomethane Structure

186581-53-3

diazomethane

4-methoxy-8-[(3-methyl-2-butenyl)oxy]furo[2,3-b]quinolin-7-ol Structure

865878-28-0

4-methoxy-8-[(3...

~%

4,7-dimethoxy-8-(3-methylbut-2-enoxy)furo[2,3-b]quinoline Structure

81536-07-4

4,7-dimethoxy-8...

Skimmianin Structure

83-95-4

Skimmianin

~%

Haplopine Structure

5876-17-5

Haplopine

(7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-14-4

(7S,8R)-4-metho...

~%

Haplopine Structure

5876-17-5

Haplopine

4-chloro-7,8-dimethoxyfuro[2,3-b]quinoline Structure

865878-27-9

4-chloro-7,8-di...

~%

Haplopine Structure

5876-17-5

Haplopine

diazomethane Structure

186581-53-3

diazomethane

4-methoxyfuro[2,3-b]quinolin-6-ol Structure

65967-10-4

4-methoxyfuro[2...

~89%

4,6-dimethoxyfuro[2,3-b]quinoline Structure

2221-41-2

4,6-dimethoxyfu...

(5R,6S)-4-methoxy-5,6-dihydrofuro[2,3-b]quinoline-5,6-diol Structure

865878-18-8

(5R,6S)-4-metho...

~%

4,6-dimethoxyfuro[2,3-b]quinoline Structure

2221-41-2

4,6-dimethoxyfu...

(7S,8R)-4-methoxy-7,8-dihydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-14-4

(7S,8R)-4-metho...

~%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

diazomethane Structure

186581-53-3

diazomethane

Robustine Structure

2255-50-7

Robustine

~88%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

(7S,8R)-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7,8-diol Structure

865878-22-4

(7S,8R)-4-metho...

~%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

(7S,8S)-8-bromo-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-7-yl acetate Structure

865878-23-5

(7S,8S)-8-bromo...

~%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

dictamnine 7,8-oxide Structure

865878-25-7

dictamnine 7,8-oxide

~%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

(7S,8S)-5,8-dibromo-4-methoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-7-yl acetate Structure

865878-24-6

(7S,8S)-5,8-dib...

~%

gamma-Fagarine Structure

524-15-2

gamma-Fagarine

(5R,6S)-4-methoxy-5,6-dihydrofuro[2,3-b]quinoline-5,6-diol Structure

865878-18-8

(5R,6S)-4-metho...

~%

4-methoxyfuro[2,3-b]quinolin-6-ol Structure

65967-10-4

4-methoxyfuro[2...


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