Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthetic Studies of Venturicidins. Synthesis of the C1–C14 Segment of Venturicidins
Masaya NakataJunji OhashiKunihiko OhsawaToru NishimuraMitsuhiro KinoshitaKuniaki Tatsuta
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1993 Volume 66 Issue 11 Pages 3464-3474

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Abstract

The C1–C14 segment of venturicidins, (2R,6R)-3,6-dihydro-6-[(E)-7-(dimethoxyphosphinyl)-1-methyl-6-oxo-1-heptenyl]-2-methoxy-5-methyl-2H-pyran-2-acetic acid (1), has been synthesized. The C8–C13 segment of venturicidins, (E)-2-bromo-7-(4,4′-dimethoxytriphenylmethoxy)-2-heptene (2), was lithiated with t-butyllithium and the resulting vinyllithium compound was coupled with the C1–C7 segment, (2Z,7S)-7-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-2-methyl-5,5-(trimethylenedithio)-2-octenal (4), to afford the alcohol. A subsequent seven-step conversion of this alcohol furnished the synthesis of the C1–C13 segment, (2R,6R)-3,6-dihydro-6-[(E)-6-hydroxy-1-methyl-1-hexenyl]-2-methoxy-5-methyl-2H-pyran-2-acetate (9). Finally, the known four-step transformation led 9 to the target compound 1.

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© 1993 The Chemical Society of Japan
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