A Diels-Alder Approach to the Pyridine C Ring of Streptonigrin

Deukjoon Kim; Steven M. Weinreb

doi:10.1021/jo00395a029

A Diels-Alder Approach to the Pyridine C Ring of Streptonigrin

Deukjoon Kim, Steven M. Weinreb

Chemistry

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23 Scopus citations

Abstract

A model synthetic approach to synthesis of the pyridine C ring of the antitumor agent and antibiotic streptonigrin (1) is described. A hetero-Diels-Alder reaction is used as the method of ring construction. Studies of the reaction of dienophile 6 with dienes 13-16 and 18 are described in detail, particularly in regard to regioselectivity. A mechanistic model is proposed to rationalize the results. Adduct 27 has been converted to an acetylpyridine 42, which possesses four of the five substituents present in the desired streptonigrin synthon 3.

Original language	English (US)
Pages (from-to)	121-125
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	43
Issue number	1
DOIs	https://doi.org/10.1021/jo00395a029
State	Published - Jan 1 1978

All Science Journal Classification (ASJC) codes

Organic Chemistry

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abstract = "A model synthetic approach to synthesis of the pyridine C ring of the antitumor agent and antibiotic streptonigrin (1) is described. A hetero-Diels-Alder reaction is used as the method of ring construction. Studies of the reaction of dienophile 6 with dienes 13-16 and 18 are described in detail, particularly in regard to regioselectivity. A mechanistic model is proposed to rationalize the results. Adduct 27 has been converted to an acetylpyridine 42, which possesses four of the five substituents present in the desired streptonigrin synthon 3.",

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N2 - A model synthetic approach to synthesis of the pyridine C ring of the antitumor agent and antibiotic streptonigrin (1) is described. A hetero-Diels-Alder reaction is used as the method of ring construction. Studies of the reaction of dienophile 6 with dienes 13-16 and 18 are described in detail, particularly in regard to regioselectivity. A mechanistic model is proposed to rationalize the results. Adduct 27 has been converted to an acetylpyridine 42, which possesses four of the five substituents present in the desired streptonigrin synthon 3.

AB - A model synthetic approach to synthesis of the pyridine C ring of the antitumor agent and antibiotic streptonigrin (1) is described. A hetero-Diels-Alder reaction is used as the method of ring construction. Studies of the reaction of dienophile 6 with dienes 13-16 and 18 are described in detail, particularly in regard to regioselectivity. A mechanistic model is proposed to rationalize the results. Adduct 27 has been converted to an acetylpyridine 42, which possesses four of the five substituents present in the desired streptonigrin synthon 3.

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A Diels-Alder Approach to the Pyridine C Ring of Streptonigrin

Abstract

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