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21st August 2013 @ 13:41

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Reaction information

*#Reaction file  
*Reaction file type CDX

 General procedure D (see below) with diene 123c (100 mg, 0.27 mmol) and N‑phenylmaleimide (69.2 mg, 0.29 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as a white solid (117 mg, 79%).


General procedure D:

The appropriate dienophile (1.1 eq.) was added to diene 123a,c or j (1 eq.) in benzene (1.00 mL). The reaction mixture was heated at reflux for 16 h. The solvent was removed in vacuo to give the crude product, which was purified as described.


*Yield (%)  79
*Type of Yield Isolated product yield
AH Thesis_2011_pp100.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 130c: endo-8-Butyl-6-phenyl-1-tosyl-4-(trimethylsilyl)-2,3,4,4a,7a,8-hexahydropyrrolo[3,4-f]indole-5,7(1H,6H)-dione

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Overall reaction? True
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For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp100.pdf
AH Thesis_2011_pp176-223.pdf