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Skeletal transformation of podocarpic acid type diterpene.

✍ Scribed by Akira Tahara; Tomihiko Ohsawa

Book ID
104239518
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
155 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

In our research course on the chemical transformation of the representative diterpenes, as resin acids, their skeletal conversion has aroused our interest and has been undertaken since a few years ago.

Previously, aldol condensation of dioxo ester (II) obtained from methyl tetra-. hydro-deoxy-enantio-podocarpate (I) by oxidative cleavage of its B/C-ring juncture,

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Transformation of the diterpene A/B ring
Transformation of the diterpene A/B ring juncture to the antipodal system. The synthesis of (-)-podocarpic acid from (+)-dehydroabietic acid.
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This paper describes a simple two-step sequence involving the catalytic inversion of the steroidaltype A/B ring juncture to an antipodal A/B ring juncture. This procedure has been employed in the synthesis of (-)-podocarpic acid (enontiopodocarpic acid) from (+)-dehydroabietic acid. Skeletons having

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