A General Synthetic Approach to the (20S)??Camptothecin Family of Antitumor Agents by a Regiocontrolled Cascade Radical Cyclization of Aryl Isonitriles

H Josien, SB Ko, D Bom…

Index: Josien, Hubert; Ko, Sung-Bo; Bom, David; Curran, Dennis P. Chemistry - A European Journal, 1998 , vol. 4, # 1 p. 67 - 83

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Citation Number: 183

Abstract

Abstract The power of radical reactions continues to increase! A cascade radical annulation route now allows perhaps the mildest and most general method for the synthesis of both known and new members of the camptothecin family (parent structure on the right) of antitumor agents.

 Related Synthetic Route
(S)-4,11-Diethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

86639-53-4

(S)-4,11-Diethy...

~92%

7-Ethyl-10-hydroxycamptothecin Structure

86639-52-3

7-Ethyl-10-hydr...

(20S)-10,11-methylenedioxy-12-trimethylsilylcamptothecin Structure

202745-09-3

(20S)-10,11-met...

~78%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

piperonal Structure

120-57-0

piperonal

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

(S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone Structure

173442-34-7

(S)-4-ethyl-4-h...

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-propargyl-1H-pyrano[3,4-c]-8-pyridone Structure

174092-80-9

(S)-4-Ethyl-4-h...

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

(S)-4-Ethyl-4-hydroxy-6-iodo-8-Methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one Structure

174092-79-6

(S)-4-Ethyl-4-h...

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

4-(trimethylsilyl)benzo[d][1,3]dioxole-5-carbaldehyde Structure

181780-65-4

4-(trimethylsil...

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

(+/-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one Structure

869097-09-6

(+/-)-4-ethyl-4...

~%

10,11-methylenedioxycamptothecin Structure

135415-73-5

10,11-methylene...

1-(3-Aminophenyl)ethanol Structure

2454-37-7

1-(3-Aminopheny...

Ethyl formate Structure

109-94-4

Ethyl formate

~%

Formamide, N-[3-(1-hydroxyethyl)phenyl]- (9CI) Structure

321898-62-8

Formamide, N-[3...

N/A Structure

1197040-29-1

N/A

(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-propargyl-1H-pyrano[3,4-c]-8-pyridone Structure

174092-80-9

(S)-4-Ethyl-4-h...

~61%

Campathecin Structure

7689-03-4

Campathecin

N/A Structure

1197040-29-1

N/A

(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-allyl-1H-pyrano[3,4-c]-8-pyridone Structure

202745-20-8

(S)-4-Ethyl-4-h...

~20%

Campathecin Structure

7689-03-4

Campathecin

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

19685-10-0

(4S)-4-Ethyl-4-...

~84%

(S)-10-Hydroxycamptothecin Structure

19685-09-7

(S)-10-Hydroxyc...

(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(2-pentynyl)-1H-pyrano[3,4-c]-8-pyridone Structure

174092-83-2

(S)-4-Ethyl-4-h...

[1,4'] Bipiperidinyl-1'-carboxylic acid 4-isonitrilo-phenylester Structure

202744-81-8

[1,4'] Bipiperi...

~31%

Irinotecan Structure

97682-44-5

Irinotecan

N/A Structure

202745-28-6

N/A

~85%

9-amino-20-camptothecin Structure

86639-63-6

9-amino-20-camp...


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