An Efficient Synthesis of γ-Methylene-γ-butyrolactone (α'-Angelicalactone). Application to the Synthesis of Deoxyobtusilactone and Deoxyisoobtusilactone

Richard A. Amos; John A. Katzenellenbogen

doi:10.1021/jo00398a007

An Efficient Synthesis of γ-Methylene-γ-butyrolactone (α'-Angelicalactone). Application to the Synthesis of Deoxyobtusilactone and Deoxyisoobtusilactone

Richard A. Amos, John A. Katzenellenbogen

Chemistry

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

Abstract

The mercury(II)-catalyzed cyclization of 4-pentynoic acid proceeds efficiently to give γ-methylene-γ-butyrolac-tone (α'-angelicalactone). The enolate of this lactone reacts with 11-dodecenal producing separable diastereomeric β-hydroxylactones. The corresponding methanesulfonate derivatives undergo partially selective elimination to afford deoxyobtusilactone and deoxyisoobtusilactone.

Original language	English (US)
Pages (from-to)	560-564
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	43
Issue number	4
DOIs	https://doi.org/10.1021/jo00398a007
State	Published - 1978

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00398a007

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abstract = "The mercury(II)-catalyzed cyclization of 4-pentynoic acid proceeds efficiently to give γ-methylene-γ-butyrolac-tone (α'-angelicalactone). The enolate of this lactone reacts with 11-dodecenal producing separable diastereomeric β-hydroxylactones. The corresponding methanesulfonate derivatives undergo partially selective elimination to afford deoxyobtusilactone and deoxyisoobtusilactone.",

author = "Amos, {Richard A.} and Katzenellenbogen, {John A.}",

year = "1978",

doi = "10.1021/jo00398a007",

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pages = "560--564",

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AU - Katzenellenbogen, John A.

PY - 1978

Y1 - 1978

N2 - The mercury(II)-catalyzed cyclization of 4-pentynoic acid proceeds efficiently to give γ-methylene-γ-butyrolac-tone (α'-angelicalactone). The enolate of this lactone reacts with 11-dodecenal producing separable diastereomeric β-hydroxylactones. The corresponding methanesulfonate derivatives undergo partially selective elimination to afford deoxyobtusilactone and deoxyisoobtusilactone.

AB - The mercury(II)-catalyzed cyclization of 4-pentynoic acid proceeds efficiently to give γ-methylene-γ-butyrolac-tone (α'-angelicalactone). The enolate of this lactone reacts with 11-dodecenal producing separable diastereomeric β-hydroxylactones. The corresponding methanesulfonate derivatives undergo partially selective elimination to afford deoxyobtusilactone and deoxyisoobtusilactone.

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An Efficient Synthesis of γ-Methylene-γ-butyrolactone (α'-Angelicalactone). Application to the Synthesis of Deoxyobtusilactone and Deoxyisoobtusilactone

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