Journal of Organic Chemistry p. 2355 - 2361 (1990)
Update date:2022-07-29
Topics:
Caldwell
Rupprecht
Bondy
Davis
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 boronic ester 17 to control two chiral centers. The enolate of the chiral dioxolanone 6 condensed with lactone 7 to produce the complete 14-carbon skeleton as a single diastereomer.
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