Synthesis of the lipophilic side chain of the cyclic hexadepsipeptide antibiotic L-156,602

CG Caldwell, KM Rupprecht, SS Bondy…

Index: Caldwell; Rupprecht; Bondy; Davis Journal of Organic Chemistry, 1990 , vol. 55, # 8 p. 2355 - 2361

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Citation Number: 30

Abstract

The 14-carbon tetrahydropyranylpropionic acid side chain of the cyclic hexadepsipeptide antibiotic L-156,602 (1) has been prepared as the methyl ester derivative 5. Asymmetric synthesis of the key intermediate 11-carbon lactone 7 was accomplished using diastereoselective alkylation of the alkoxide enolate of methyl (R)-3-hydroxybutanoate. A second route to lactone 7 utilized sequential organometallic reactions of the pinanediol ...

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