SYNTHESIS OF (-)-HELIANNUOL E VIA MERCURIC TRIFLATE CATALYZED ARYLENE CYCLIZATION

被引：10

作者：

Kamei, Tomoyo ^{[1
,2
]}

Takahashi, Tamiko ^{[2
]}

Yoshida, Masahiro ^{[1
]}

Shishido, Kozo ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[2] Josai Int Univ, Fac Pharmaceut Sci, Chiba 2838555, Japan

来源：

HETEROCYCLES | 2009年 / 78卷 / 06期

关键词：

Heliannuol E; Total Synthesis; Mercuric Triflate; Arylene Cyclization; Catalytic Reaction; BIOACTIVE SESQUITERPENE; HELIANNUOL-E; ALCOHOLS; ACID;

D O I：

10.3987/COM-09-11649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The third-generation synthesis of (-)-heliannuol E has been accomplished employing mercuric triflate catalyzed arylene cyclization as the key step.

引用

页码：1439 / 1444

页数：6

共 16 条

[1] Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation
Crimmins, MT
Emmitte, KA
Katz, JD
[J]. ORGANIC LETTERS, 2000, 2 (14) : 2165 - 2167
[2] Doi F, 2003, SYNLETT, P411
[3] SYNTHESIS OF THE CYCLIC HEXAPEPTIDE ECHINOCANDIN-D - NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ALPHA-AMINO-ACIDS
EVANS, DA
WEBER, AE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) : 7151 - 7157
[4] A novel B(C6F5)3-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes
Gevorgyan, V
Rubin, M
Benson, S
Liu, JX
Yamamoto, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6179 - 6186
[5] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS
GRIECO, PA
GILMAN, S
NISHIZAWA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) : 1485 - 1486
[6] Synthetic studies on nogarol anthracyclines. Enantioselective total synthesis of an aminohydroxy epoxybenzoxocin
Hauser, FM
Ganguly, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) : 1842 - 1849
[7] First asymmetric syntheses of 6-substituted nipecotic acid derivatives
Hoesl, CE
Höfner, G
Wanner, KT
[J]. TETRAHEDRON, 2004, 60 (02) : 307 - 318
[8] Asymmetric total syntheses of (+)-3-(Z)-laureatin and (+)-3-(Z)-isolaureatin by "lone pair-lone pair interaction-controlled" isomerization
Kim, Hyoungsu
Lee, Hyunjoo
Lee, Dongjoo
Kim, Sanghee
Kim, Deukjoon
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) : 2269 - 2274
[9] Heliannuol E.: A novel bioactive sesquiterpene of the heliannane family
Macías, FA
Varela, RM
Torres, A
Molinillo, JMG
[J]. TETRAHEDRON LETTERS, 1999, 40 (25) : 4725 - 4728
[10] Hg(OTf)2-catalyzed arylene cyclization
Namba, Kosuke
Yamamoto, Hirofumi
Sasaki, Ikuo
Mori, Kumiko
Imagawa, Hiroshi
Nishizawa, Mugio
[J]. ORGANIC LETTERS, 2008, 10 (09) : 1767 - 1770

← 1 2 →