SYNTHESIS OF (-)-INDOLACTAM-V

M  MASCAL; C J  MOODY; A M Z  SLAWIN; D J  WILLIAMS

SYNTHESIS OF (-)-INDOLACTAM-V

M MASCAL, C J MOODY, A M Z SLAWIN, D J WILLIAMS

Research output: Contribution to journal › Article › peer-review

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-isopropyl-pyrrolo[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
Pages (from-to)	823-830
Number of pages	8
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	7
Publication status	Published - 7 Apr 1992

Keywords

TUMOR PROMOTERS TELEOCIDINS
BIOSYNTHESIS
REQUIREMENTS
LYNGBYATOXIN
MODULATORS

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@article{4205443701cd4015b53376285c8bfefc,

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-isopropyl-pyrrolo[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.",

keywords = "TUMOR PROMOTERS TELEOCIDINS, BIOSYNTHESIS, REQUIREMENTS, LYNGBYATOXIN, MODULATORS",

author = "M MASCAL and MOODY, {C J} and SLAWIN, {A M Z} and WILLIAMS, {D J}",

year = "1992",

month = apr,

day = "7",

language = "English",

pages = "823--830",

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

issn = "0300-922X",

publisher = "Chemical Society",

number = "7",

}

TY - JOUR

T1 - SYNTHESIS OF (-)-INDOLACTAM-V

AU - MASCAL, M

AU - MOODY, C J

AU - SLAWIN, A M Z

AU - WILLIAMS, D J

PY - 1992/4/7

Y1 - 1992/4/7

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-isopropyl-pyrrolo[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-isopropyl-pyrrolo[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.

KW - TUMOR PROMOTERS TELEOCIDINS

KW - BIOSYNTHESIS

KW - REQUIREMENTS

KW - LYNGBYATOXIN

KW - MODULATORS

M3 - Article

SN - 0300-922X

SP - 823

EP - 830

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 7

ER -

SYNTHESIS OF (-)-INDOLACTAM-V

Abstract

Keywords

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