Total Synthesis of the Proposed Structure for Chaunopyran A and Its Absolute Configuration

Total Synthesis of the Proposed Structure for Chaunopyran A and Its Absolute Configuration
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Chaunopyran A 的拟议结构的全合成及其绝对构型

DOI:
10.1021/acs.jnatprod.0c00552
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发表时间:
2020
期刊:
影响因子:
5.1
通讯作者:
Takahashi S.
Takahashi S.
中科院分区:
生物学2区
文献类型:
--
作者:
Ogawa N.;Mamada S.;Hama T.;Koshino H.;Takahashi S.

文献摘要

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本文介绍了一个七步合成的建议结构的chaunopyran A产生的共培养aChaunopycnissp。和钩状木霉(Trichoderma hamatum)。该合成包括作为关键步骤的二烯砜和四氢吡喃醛的偶联。合成样品的比旋光度值与天然产物的比旋光度值符号相反,表明天然产物的绝对构型应作修正。
This paper describes a seven-step synthesis of the proposed structure for chaunopyran A produced by cocultivation of aChaunopycnissp. andTrichoderma hamatum. This synthesis included a coupling of a diene sulfone and a tetrahydropyranyl aldehyde as a key step. The sign of the specific rotation value of the synthetic sample was opposite that of the natural product, suggesting that the absolute configuration of the natural product should be revised.