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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者10.1002/anie.201600521

Total synthesis of (.+-.)-aphidicolin and (.+-.)-. beta.-chamigrene

…, WC Dow, JD Godfrey, S Thaisrivongs

文献索引：Ireland, Robert E.; Dow, William C.; Godfrey, Jollie D.; Thaisrivongs, Suvit Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1001 - 1013

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被引用次数: 47

摘要

Total syntheses of (f)-chamigrene and (*)-aphidicolin are described. Both approaches are based on the spiroannelation of related a-methylene ketones through first hetero-Diels-Alder condensation and then Claisen rearrangement of the derived allyl vinyl ethers. A central feature of the (f)-aphidicolin synthesis is the rearrangement of the intermediate ((trimethylsily1) methyl) cyclobutanone 16 to the aphidicolane bicyclo [3.2. l] octane ring ...

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~81%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

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2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~0%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

未登录结构式

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

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3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

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2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

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2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

1,7,7-trimethylcycloheptene结构式

1,7,7-trimethyl...

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5-amino-3-(5-amino-4-cyano-3-methylfuran-2-yl)-3-methyl-2H-furan-4-carbothioamide结构式

5-amino-3-(5-am...

甲基三苯基溴化膦结构式

甲基三苯基溴化膦

~%

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

1,7,7-trimethylcycloheptene结构式

1,7,7-trimethyl...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

1,7,7-trimethylcycloheptene结构式

1,7,7-trimethyl...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

1-叔丁基-1-环己烯结构式

1-叔丁基-1-环己烯

1,1-dimethyl-2-methylidenecycloheptane结构式

1,1-dimethyl-2-...

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

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Methyl 3-(dimethylamino)-2-((trimethylsilyl)methyl)propionat结构式

Methyl 3-(dimet...

~78%

methyl 2-(trimethylsilylmethyl)prop-2-enoate结构式

methyl 2-(trime...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

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3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

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2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

查看详情

甲基三苯基溴化膦结构式

甲基三苯基溴化膦

2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

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硝酸异戊酯结构式

硝酸异戊酯

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

~45%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

查看详情

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

~%

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

查看详情

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

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1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

~%

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

查看详情

methyl 5,5,9-trimethylspiro[5.5]undec-9-ene-1-carboxylate结构式

methyl 5,5,9-tr...

~93%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

1,2,2-trimethylcycloheptanol结构式

1,2,2-trimethyl...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

3,3-dimethyl-2-methylidenecycloheptan-1-one结构式

3,3-dimethyl-2-...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

2-ethenyl-2,5,5-trimethyl-3,4,6,7,8,9-hexahydrocyclohepta[b]pyran结构式

2-ethenyl-2,5,5...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

2,5,5-trimethyl-2,3,4,5,6,7,8,9-octahydrocyclohepta[b]pyran-2-carbaldehyde结构式

2,5,5-trimethyl...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

2,5,5-Trimethyl-3,4,6,7,8,9-hexahydro-cyclohepta(b)pyran-2-carboxylic Acid, Methyl Ester结构式

2,5,5-Trimethyl...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

3,12,12-trimeth...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

8-hydroxyimino-3,12,12-trimethylspiro[5.6]dodec-3-en-7-one结构式

8-hydroxyimino-...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情

8-diazonio-3,12,12-trimethylspiro[5.6]dodeca-3,7-dien-7-olate结构式

8-diazonio-3,12...

~%

(5,5,9-trimethylspiro[5.5]undec-9-en-1-yl)methanol结构式

(5,5,9-trimethy...

查看详情