Volume 25, Issue 42
Natural Products
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ChemInform Abstract: Synthesis of (-)-Bactobolin from D-Glucose and from (+)-Actinobolin.

D. E. WARD

D. E. WARD

Dep. Chem., Univ. Sask., Saskatoon, Sask. S7N 0W0, Can.

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Y. GAI

Y. GAI

Dep. Chem., Univ. Sask., Saskatoon, Sask. S7N 0W0, Can.

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B. F. KALLER

B. F. KALLER

Dep. Chem., Univ. Sask., Saskatoon, Sask. S7N 0W0, Can.

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First published: October 18, 1994

Abstract

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ChemInform Abstract

Starting from (D)-glucose (I) or (+)-actinobolin (III) the synthesis of an important intermediate (X) for preparing enantiospecifically (-)- bactobolin (XI) (broad spectrum antibiotic with antitumor activity) is carried out. Key step is the diastereoselective addition of in-situ formed dichloromethyl lithium (VI) to the keto derivative (V) in the presence of cerium chloride via two different reaction pathways.

chemical structure image

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