Asymmetric synthesis of (-)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

Bo Liu; Ming-Jung Chen; Ching-Yu Lo; Rai-Shung Liu

doi:10.1016/S0040-4039(01)00189-7

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Asymmetric synthesis of (-)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

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Asymmetric synthesis of (-)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

Bo Liu, Ming-Jung Chen, Ching-Yu Lo and Rai-Shung Liu

Tetrahedron Letters, Vol.42(13), pp.2533-2535

26/03/2001

DOI: https://doi.org/10.1016/S0040-4039(01)00189-7

Abstract

Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. © 2001 Elsevier Science Ltd.

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Title: Asymmetric synthesis of (-)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction
Creators - without role: Bo Liu - National Tsing Hua University
Ming-Jung Chen - Department of Chemistry , National Tsing-Hua University
Ching-Yu Lo - Department of Chemistry , National Tsing-Hua University
Rai-Shung Liu - Department of Chemistry , National Tsing-Hua University
Publication Details: Tetrahedron Letters, Vol.42(13), pp.2533-2535
Identifiers: 9957774022106774
Academic Unit: Department of Chemistry, College of Science, National Tsing Hua University
Language: English
Resource Type: Journal article

Asymmetric synthesis of (-)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

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