Stereoselective synthesis of marine antibiotic (-)-malyngolide and its stereoisomers.

Article abstract of DOI:10.1080/00021369.1990.10869988

A convenient synthetic method for the marine antibiotic (-)-malyngolide and its stereoisomers was accomplished from a chiral alpha-alkoxyketone (4), which was readily available as a chiron. Chiral quaternary carbon synthons (5a) and (5b) as the key intermediates were constructed by the chelation controlled addition of Grignard reagent to 4. The diastereomeric mixture of 5a and 5b was readily transformed into a separable mixture of lactones (7a) and (7b), each of which could be easily separated by silica-gel column chromatography. (-)-Malyngolide and its three stereoisomers were obtained in optically pure form without the need for optical resolution.

Full text of DOI:10.1080/00021369.1990.10869988

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Agricultural and Biological Chemistry
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Stereoselective Synthesis of Marine
Antibiotic (-)-Malyngolide and Its
Stereoisomers
a
a
a
a
Itsuo Ichimoto , Kozo Machiya , Mitsunori Kirihata & Hiroo Ueda
a
Department of Agricultural Chemistry, College of Agriculture,
University of Osaka Prefecture, Sakai, Osaka 591, Japan
Published online: 08 Sep 2014.
To cite this article: Itsuo Ichimoto, Kozo Machiya, Mitsunori Kirihata & Hiroo Ueda (1990)
Stereoselective Synthesis of Marine Antibiotic (-)-Malyngolide and Its Stereoisomers, Agricultural
and Biological Chemistry, 54:3, 657-662
To link to this article: http://dx.doi.org/10.1080/00021369.1990.10869988
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