Synthesis of the marine dibromooxoindoline convolutamydine C

CS Miah; CJ Moody; IC Richards; Alexandra Martha Zoya Slawin

doi:10.1039/a700683g

Synthesis of the marine dibromooxoindoline convolutamydine C

CS Miah, CJ Moody, IC Richards, Alexandra Martha Zoya Slawin

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

Abstract

A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.

Original language	English
Pages (from-to)	2405-2412
Number of pages	8
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	16
DOIs	https://doi.org/10.1039/a700683g
Publication status	Published - 21 Aug 1997

Keywords

CARBOMETHOXY-ALPHA-DIAZOACETANILIDES
BRYOZOAN AMATHIA-CONVOLUTA
NATURAL-PRODUCTS
CHEMOSELECTIVITY
SUBSTITUENT
CARBENOIDS
INSERTION
OXIDATION
REAGENT

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1039/a700683g

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title = "Synthesis of the marine dibromooxoindoline convolutamydine C",

abstract = "A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.",

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author = "CS Miah and CJ Moody and IC Richards and Slawin, {Alexandra Martha Zoya}",

year = "1997",

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doi = "10.1039/a700683g",

language = "English",

pages = "2405--2412",

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

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T1 - Synthesis of the marine dibromooxoindoline convolutamydine C

AU - Miah, CS

AU - Moody, CJ

AU - Richards, IC

AU - Slawin, Alexandra Martha Zoya

PY - 1997/8/21

Y1 - 1997/8/21

N2 - A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.

AB - A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.

KW - CARBOMETHOXY-ALPHA-DIAZOACETANILIDES

KW - BRYOZOAN AMATHIA-CONVOLUTA

KW - NATURAL-PRODUCTS

KW - CHEMOSELECTIVITY

KW - SUBSTITUENT

KW - CARBENOIDS

KW - INSERTION

KW - OXIDATION

KW - REAGENT

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U2 - 10.1039/a700683g

DO - 10.1039/a700683g

M3 - Article

SN - 0300-922X

SP - 2405

EP - 2412

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 16

ER -

Synthesis of the marine dibromooxoindoline convolutamydine C

Abstract

Keywords

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