Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

Fuminao Doi; Takahisa Ogamino; Takeshi Sugai; Shigeru Nishiyama

doi:10.1016/S0040-4039(03)01094-3

Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

Fuminao Doi, Takahisa Ogamino, Takeshi Sugai, Shigeru Nishiyama

School of Pharmaceutical Sciences

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

37 Citations (Scopus)

Abstract

Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.

Original language	English
Pages (from-to)	4877-4880
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4039(03)01094-3
Publication status	Published - 2003 Jun 23

Keywords

Allelopathy
Heliannuol E
Helianthus annuus L. cv. SH-222
Phenolic oxidation
Ring expansion
Spirodienone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01094-3

Cite this

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title = "Enantioselective synthesis of heliannuol E; structural consideration of natural molecule",

abstract = "Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.",

keywords = "Allelopathy, Heliannuol E, Helianthus annuus L. cv. SH-222, Phenolic oxidation, Ring expansion, Spirodienone",

author = "Fuminao Doi and Takahisa Ogamino and Takeshi Sugai and Shigeru Nishiyama",

note = "Funding Information: This work was supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, as well as Keio Gijyuku Fund for the Advancement of Education and Research. The authors are indebted to Dr. M. Tsuchimoto and Mr. N. Kutsumura for the X-ray crystallographic analysis.",

year = "2003",

month = jun,

day = "23",

doi = "10.1016/S0040-4039(03)01094-3",

language = "English",

volume = "44",

pages = "4877--4880",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "26",

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T1 - Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

AU - Doi, Fuminao

AU - Ogamino, Takahisa

AU - Sugai, Takeshi

AU - Nishiyama, Shigeru

N1 - Funding Information: This work was supported by Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, as well as Keio Gijyuku Fund for the Advancement of Education and Research. The authors are indebted to Dr. M. Tsuchimoto and Mr. N. Kutsumura for the X-ray crystallographic analysis.

PY - 2003/6/23

Y1 - 2003/6/23

N2 - Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.

AB - Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.

KW - Allelopathy

KW - Heliannuol E

KW - Helianthus annuus L. cv. SH-222

KW - Phenolic oxidation

KW - Ring expansion

KW - Spirodienone

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U2 - 10.1016/S0040-4039(03)01094-3

DO - 10.1016/S0040-4039(03)01094-3

M3 - Article

AN - SCOPUS:0037565122

SN - 0040-4039

VL - 44

SP - 4877

EP - 4880

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

Abstract

Keywords

ASJC Scopus subject areas

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