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Article

First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans: Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

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Shin-ichi Yoshida, Tsuyoshi Ogiku, Hiroshi Ohmizu,* and Tameo Iwasaki

Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa, Osaka 532, Japan

J. Org. Chem., 1997, 62 (5), pp 1310–1316

DOI: 10.1021/jo961733y

Publication Date (Web): March 7, 1997

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial−equatorial 1, diequatorial 2, and diaxial 3 types of this series.

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Published In Issue March 07, 1997
Received September 10, 1996

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Article

First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans: Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

Abstract

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History

Recommend & Share

Related Content

Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry: NMR Studies of Amino Acid-Derived Organozinc Reagents

Practical Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols in 2,4,6-Collidine Leading to α,β-Unsaturated Lactones: Concise Stereoselective Synthesis of (+)-Isomintlactone

Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles

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