Abstract
A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropylpyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 823-830 |
| Number of pages | 8 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 7 |
| State | Published - 1992 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
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Synthesis of (-)-indolactam V. / Mascal, Mark; Moody, Christopher J.; Slawin, Alexandra M Z; Williams, David J.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 7, 1992, p. 823-830.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of (-)-indolactam V
AU - Mascal, Mark
AU - Moody, Christopher J.
AU - Slawin, Alexandra M Z
AU - Williams, David J.
PY - 1992
Y1 - 1992
N2 - A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropylpyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.
AB - A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropylpyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.
UR - http://www.scopus.com/inward/record.url?scp=37049070292&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37049070292&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049070292
SP - 823
EP - 830
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1470-4358
IS - 7
ER -