Synthesis of the Right‐Side Structure of Type B Physalins

Masaki Morita, Shuntaro Kojima, Megumi Ohkubo, Hiroyuki Koshino, Daisuke Hashizume, Go Hirai, Keiji Maruoka, Mikiko Sodeoka

Research output: Contribution to journalArticle

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Abstract

We present a full account of our synthetic studies on the racemic DEFGH-ring moiety of physalins, featuring domino ring transformation of a tricyclic key intermediate. We also report the results of a detailed mechanistic examination of the domino ring transformation, as well as a reoptimization of the 2,3-Wittig rearrangement and methylation steps. Furthermore, we have newly established a method for the preparation of an optically active synthetic intermediate by enzymatic kinetic resolution. Our work provides access to both natural and nonnatural right-side physalin structures.
Original languageEnglish
Pages (from-to)309-318
Number of pages10
JournalIsrael Journal of Chemistry
Volume57
Issue number3-4
DOIs
Publication statusPublished - 2017

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Methylation
Kinetics
physalin B

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Morita, M., Kojima, S., Ohkubo, M., Koshino, H., Hashizume, D., Hirai, G., ... Sodeoka, M. (2017). Synthesis of the Right‐Side Structure of Type B Physalins. Israel Journal of Chemistry, 57(3-4), 309-318. https://doi.org/10.1002/ijch.201600110

Synthesis of the Right‐Side Structure of Type B Physalins. / Morita, Masaki; Kojima, Shuntaro; Ohkubo, Megumi; Koshino, Hiroyuki; Hashizume, Daisuke; Hirai, Go; Maruoka, Keiji; Sodeoka, Mikiko.

In: Israel Journal of Chemistry, Vol. 57, No. 3-4, 2017, p. 309-318.

Research output: Contribution to journalArticle

Morita, M, Kojima, S, Ohkubo, M, Koshino, H, Hashizume, D, Hirai, G, Maruoka, K & Sodeoka, M 2017, 'Synthesis of the Right‐Side Structure of Type B Physalins', Israel Journal of Chemistry, vol. 57, no. 3-4, pp. 309-318. https://doi.org/10.1002/ijch.201600110
Morita, Masaki ; Kojima, Shuntaro ; Ohkubo, Megumi ; Koshino, Hiroyuki ; Hashizume, Daisuke ; Hirai, Go ; Maruoka, Keiji ; Sodeoka, Mikiko. / Synthesis of the Right‐Side Structure of Type B Physalins. In: Israel Journal of Chemistry. 2017 ; Vol. 57, No. 3-4. pp. 309-318.
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