Synthesis of (-)-indolactam V

Mark Mascal; Christopher J. Moody; Alexandra M Z Slawin; David J. Williams

Synthesis of (-)-indolactam V

Mark Mascal, Christopher J. Moody, Alexandra M Z Slawin, David J. Williams

Research output: Contribution to journal › Article

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

ASJC Scopus subject areas

Chemistry(all)

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title = "Synthesis of (-)-indolactam V",

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.",

author = "Mark Mascal and Moody, {Christopher J.} and Slawin, {Alexandra M Z} and Williams, {David J.}",

year = "1992",

language = "English (US)",

pages = "823--830",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1470-4358",

publisher = "Chemical Society",

number = "7",

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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.

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JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

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