Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Stereochemical Studies. XLII. Asymmetric Synthesis of naturally Occurring Podocarpic Acid
TAKANORI SONESHIRO TERASHIMASHUNICHI YAMADA
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1976 Volume 24 Issue 6 Pages 1288-1292

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Abstract
Optically active methyl deoxypodocarpate ((S) (+)-5b), 92% optically pure, was synthesized from (R) (+)-δ-ketoaldehyde ((R) (-)-3a) which was obtainable by the asymmetric synthesis using D-proline-derived pyrrolidine ((R)-4 (R2=CH2NC4H3)) as a chiral additive. The chemical scheme which was previously developed, was used for the conversion of (R) (-)-3a to (S) (+)-phenanthrone derivative ((S) (+)-1a), and a combination of reductive carbomethoxylation and reductive alkylation was adopted for preparing (S) (+)-5b from (S) (+)-1a. Since (S) (+)-5b had already been converted to naturally occurring podocarpic acid ((S) (+)-5a), the asymmetric synthesis of (S) (+)-5a was accomplished.
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© The Pharmaceutical Society of Japan
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