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

doi:10.1002/ijch.201600110

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

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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 language	English
Pages (from-to)	309-318
Number of pages	10
Journal	Israel Journal of Chemistry
Volume	57
Issue number	3-4
DOIs	https://doi.org/10.1002/ijch.201600110
Publication status	Published - 2017

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10.1002/ijch.201600110

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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.",

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

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AU - Morita, Masaki

AU - Kojima, Shuntaro

AU - Ohkubo, Megumi

AU - Koshino, Hiroyuki

AU - Hashizume, Daisuke

AU - Hirai, Go

AU - Maruoka, Keiji

AU - Sodeoka, Mikiko

PY - 2017

Y1 - 2017

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AB - 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.

U2 - 10.1002/ijch.201600110

DO - 10.1002/ijch.201600110

M3 - Article

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VL - 57

SP - 309

EP - 318

JO - Israel Journal of Chemistry

JF - Israel Journal of Chemistry

IS - 3-4

ER -

Synthesis of the Right‐Side Structure of Type B Physalins

Abstract

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