Synthesis of oxygenated eremophilanes, gigantenone, phomenone and phaseolinone, phytotoxins from pathogenic fungi

Takeshi Kitahara; Hiromasa Kiyota; Hitoshi Kurata; Kenji Mori

doi:10.1016/S0040-4020(01)96908-X

Synthesis of oxygenated eremophilanes, gigantenone, phomenone and phaseolinone, phytotoxins from pathogenic fungi

Takeshi Kitahara, Hiromasa Kiyota, Hitoshi Kurata, Kenji Mori

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

24 Citations (Scopus)

Abstract

Stereoselective synthesis of several oxygenated eremophilane sesquiterpenes as phytotoxins, (+)-gigantenone 1, (+)-phomenone 2 and (+)-phaseolinone 3, was achieved in short steps from (+)-sporogen-AO 1 (13-desoxyphomenone) 4.

Original language	English
Pages (from-to)	1649-1654
Number of pages	6
Journal	Tetrahedron
Volume	47
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4020(01)96908-X
Publication status	Published - 1991
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)96908-X

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@article{dd3fd92bc24a4bd6830d8324624bfad6,

title = "Synthesis of oxygenated eremophilanes, gigantenone, phomenone and phaseolinone, phytotoxins from pathogenic fungi",

abstract = "Stereoselective synthesis of several oxygenated eremophilane sesquiterpenes as phytotoxins, (+)-gigantenone 1, (+)-phomenone 2 and (+)-phaseolinone 3, was achieved in short steps from (+)-sporogen-AO 1 (13-desoxyphomenone) 4.",

author = "Takeshi Kitahara and Hiromasa Kiyota and Hitoshi Kurata and Kenji Mori",

note = "Funding Information: WaSwashedwrth~sndbnne,dtXXl(MgSG~iilKl MlyrntrateduIy(Icyo Tbe&was w over SIC&( lg) Eluuon with hexane-EQAc (1 1-O 1) gavem 3 (7mg.0 .023mmol-.1 00%) as pnsms.m p 129-l= (BtGAc), [alDms +208” (c=O3 2, EtoH)[l~t.{\textquoteright} m p 1%128°C WAC), [aID +94.5{\textquoteright} (c=O8 , BtOH)); W &=6.0x10-smd/lI II MeOH) loge=44 (%max 243m@,C D iat 24.5”c. c=O0 24 11W1 H. Ae&,,el> -3 18(219)+, 59 50, +44 2(332),I R vmax (KBr dssk)3 540(s),3 420(m). 339Ym). 3345(m)2 990(w).2 950(w),2 880(w),1 668(s)1, 650(s)1, 455(w),1 436(w)1. 390(w).1 360(w),1 342(w). 1262(w), ml(~), 1192(w). 1174(w). 1155(w). 1111(w),1 075(w).1 056(m).1 033(s).9 98(w). 957(w). 932(w), 900(m), 890(m), 860(w), 842(w), 818(w),7 90(w).7 45(w).n o(w). 692(w)c mI, {\textquoteleft}H-NMR &3OOMH&DC&) 1.14(3H.s)1, .27(3H.d&67Hz). 143(1H,dddd&4 3, 112.123 .143 fi). 163(w). 179(1H,dq&6 7.105 Ha).2 15(lt/dddd+2&4 4.4 7.123 Hz). 2 36(lH,ddd~=28 .4 3.145 Hz), 2 Sl(lH.ddddJ=l 8.4.7.14.3.145 Ha). 264(1H,d+4 6Hz). 3 13(1H.dJ=4.6Hz). 3 62(1H,dddJ=4 4,lO 5,112Hz). 3 63(1H,s), 3 87(lItdJ=l23H+ 4 lqlH.d/=12 3Ha). S=n(lH#=18Ha). {\textquoteleft}F-NMR &22 5MHz.CDC1,) 1131,18.80,30.94,350 3.41 14, 44 45,48 81.56 75.6173.62 86.63 70.70 77, 1206 2. 1646 9, 1936 0. FoundI, 64 17: H, 7 18. Calc for &H&Is C, 6.42 7, H, 7 19 ACKNOWLEDGMENTS We UumkD r.F Sugawara,R IKEN (Inst~tutfco r physical and ChermcalR esearch).f or the generous gift of spectrald am and aubentw:s ampleaT hu work was partly supper&db y a Grant-m-w for Sclenutic Researchf rom the JapaneseM uustryo f Bclaamon,S cltncea ndc ulturea adb y l%e SankyoF oundat for thep romotiono f Lfie Scxence.",

year = "1991",

doi = "10.1016/S0040-4020(01)96908-X",

language = "English",

volume = "47",

pages = "1649--1654",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "9",

}

TY - JOUR

T1 - Synthesis of oxygenated eremophilanes, gigantenone, phomenone and phaseolinone, phytotoxins from pathogenic fungi

AU - Kitahara, Takeshi

AU - Kiyota, Hiromasa

AU - Kurata, Hitoshi

AU - Mori, Kenji

N1 - Funding Information: WaSwashedwrth~sndbnne,dtXXl(MgSG~iilKl MlyrntrateduIy(Icyo Tbe&was w over SIC&( lg) Eluuon with hexane-EQAc (1 1-O 1) gavem 3 (7mg.0 .023mmol-.1 00%) as pnsms.m p 129-l= (BtGAc), [alDms +208” (c=O3 2, EtoH)[l~t.’ m p 1%128°C WAC), [aID +94.5’ (c=O8 , BtOH)); W &=6.0x10-smd/lI II MeOH) loge=44 (%max 243m@,C D iat 24.5”c. c=O0 24 11W1 H. Ae&,,el> -3 18(219)+, 59 50, +44 2(332),I R vmax (KBr dssk)3 540(s),3 420(m). 339Ym). 3345(m)2 990(w).2 950(w),2 880(w),1 668(s)1, 650(s)1, 455(w),1 436(w)1. 390(w).1 360(w),1 342(w). 1262(w), ml(~), 1192(w). 1174(w). 1155(w). 1111(w),1 075(w).1 056(m).1 033(s).9 98(w). 957(w). 932(w), 900(m), 890(m), 860(w), 842(w), 818(w),7 90(w).7 45(w).n o(w). 692(w)c mI, ‘H-NMR &3OOMH&DC&) 1.14(3H.s)1, .27(3H.d&67Hz). 143(1H,dddd&4 3, 112.123 .143 fi). 163(w). 179(1H,dq&6 7.105 Ha).2 15(lt/dddd+2&4 4.4 7.123 Hz). 2 36(lH,ddd~=28 .4 3.145 Hz), 2 Sl(lH.ddddJ=l 8.4.7.14.3.145 Ha). 264(1H,d+4 6Hz). 3 13(1H.dJ=4.6Hz). 3 62(1H,dddJ=4 4,lO 5,112Hz). 3 63(1H,s), 3 87(lItdJ=l23H+ 4 lqlH.d/=12 3Ha). S=n(lH#=18Ha). ‘F-NMR &22 5MHz.CDC1,) 1131,18.80,30.94,350 3.41 14, 44 45,48 81.56 75.6173.62 86.63 70.70 77, 1206 2. 1646 9, 1936 0. FoundI, 64 17: H, 7 18. Calc for &H&Is C, 6.42 7, H, 7 19 ACKNOWLEDGMENTS We UumkD r.F Sugawara,R IKEN (Inst~tutfco r physical and ChermcalR esearch).f or the generous gift of spectrald am and aubentw:s ampleaT hu work was partly supper&db y a Grant-m-w for Sclenutic Researchf rom the JapaneseM uustryo f Bclaamon,S cltncea ndc ulturea adb y l%e SankyoF oundat for thep romotiono f Lfie Scxence.

PY - 1991

Y1 - 1991

N2 - Stereoselective synthesis of several oxygenated eremophilane sesquiterpenes as phytotoxins, (+)-gigantenone 1, (+)-phomenone 2 and (+)-phaseolinone 3, was achieved in short steps from (+)-sporogen-AO 1 (13-desoxyphomenone) 4.

AB - Stereoselective synthesis of several oxygenated eremophilane sesquiterpenes as phytotoxins, (+)-gigantenone 1, (+)-phomenone 2 and (+)-phaseolinone 3, was achieved in short steps from (+)-sporogen-AO 1 (13-desoxyphomenone) 4.

UR - http://www.scopus.com/inward/record.url?scp=0025978552&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025978552&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)96908-X

DO - 10.1016/S0040-4020(01)96908-X

M3 - Article

AN - SCOPUS:0025978552

SN - 0040-4020

VL - 47

SP - 1649

EP - 1654

JO - Tetrahedron

JF - Tetrahedron

IS - 9

ER -

Synthesis of oxygenated eremophilanes, gigantenone, phomenone and phaseolinone, phytotoxins from pathogenic fungi

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