Direct Methods for α-Methylene Lactone Synthesis Using Itaconic Acid Derivatives

Robert M. Carlson; Alan R. Oyler

doi:10.1021/jo00888a003

Direct Methods for α-Methylene Lactone Synthesis Using Itaconic Acid Derivatives

Robert M. Carlson, Alan R. Oyler

Chemistry & Biochemistry

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Abstract

Anions of itaconic acid derivatives [RO₂CCHC(=CH₂)CO₂] are versatile intermediates for the synthesis of α-methylene lactones. The addition of these anionic species to aldehydes or ketones and subsequent lactonization and hydrolysis have been utilized for the synthesis of a variety of compounds including protolichesterinic acid, nephrosterinic acid, and canadensolide.

Original language	English (US)
Pages (from-to)	4065-4069
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	41
Issue number	26
DOIs	https://doi.org/10.1021/jo00888a003
State	Published - Dec 1 1976

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abstract = "Anions of itaconic acid derivatives [RO2CCHC(=CH2)CO2] are versatile intermediates for the synthesis of α-methylene lactones. The addition of these anionic species to aldehydes or ketones and subsequent lactonization and hydrolysis have been utilized for the synthesis of a variety of compounds including protolichesterinic acid, nephrosterinic acid, and canadensolide.",

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N2 - Anions of itaconic acid derivatives [RO2CCHC(=CH2)CO2] are versatile intermediates for the synthesis of α-methylene lactones. The addition of these anionic species to aldehydes or ketones and subsequent lactonization and hydrolysis have been utilized for the synthesis of a variety of compounds including protolichesterinic acid, nephrosterinic acid, and canadensolide.

AB - Anions of itaconic acid derivatives [RO2CCHC(=CH2)CO2] are versatile intermediates for the synthesis of α-methylene lactones. The addition of these anionic species to aldehydes or ketones and subsequent lactonization and hydrolysis have been utilized for the synthesis of a variety of compounds including protolichesterinic acid, nephrosterinic acid, and canadensolide.

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Direct Methods for α-Methylene Lactone Synthesis Using Itaconic Acid Derivatives

Abstract

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