Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

被引:16
作者
Katoh, Naoto [1 ]
Nakahata, Takashi [1 ]
Kuwahara, Shigefumi [1 ]
机构
[1] Tohoku Univ, Grad Sch Agr Sci, Lab Appl Bioorgan Chem, Aoba Ku, Sendai, Miyagi 9818555, Japan
关键词
phthalide; take-all; total synthesis; Alder-Rickert reaction;
D O I
10.1016/j.tet.2008.07.023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9073 / 9077
页数:5
相关论文
共 26 条
[1]  
ACHENBACH H, 1985, LIEBIGS ANN CHEM, P1596
[2]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[3]   A TOTAL SYNTHESIS OF MYCOPHENOLIC ACID [J].
BIRCH, AJ ;
WRIGHT, JJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (12) :2635-+
[4]   MOLECULAR MECHANISMS OF DEFENSE BY RHIZOBACTERIA AGAINST ROOT DISEASE [J].
COOK, RJ ;
THOMASHOW, LS ;
WELLER, DM ;
FUJIMOTO, D ;
MAZZOLA, M ;
BANGERA, G ;
KIM, D .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (10) :4197-4201
[5]   HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].
COREY, EJ ;
GROSS, AW .
TETRAHEDRON LETTERS, 1984, 25 (05) :495-498
[6]   Total synthesis of forskolin .1. [J].
Delpech, B ;
Calvo, D ;
Lett, R .
TETRAHEDRON LETTERS, 1996, 37 (07) :1015-1018
[7]   A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].
DeMico, A ;
Margarita, R ;
Parlanti, L ;
Vescovi, A ;
Piancatelli, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977
[8]   Total synthesis of archaeal 36-membered macrocyclic diether lipid [J].
Eguchi, T ;
Arakawa, K ;
Terachi, T ;
Kakinuma, K .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1924-1933
[9]   Facile preparation of nucleoside-5′-carboxylic acids [J].
Epp, JB ;
Widlanski, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :293-295
[10]   A stereoselective synthesis of (2S,4R)-δ-hydroxyleucine methyl ester:: a component of cyclomarin A [J].
Hansen, DB ;
Starr, ML ;
Tolstoy, N ;
Joullié, MA .
TETRAHEDRON-ASYMMETRY, 2005, 16 (22) :3623-3627