Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain

被引：20

作者：

Adachi, Masaatsu ^{[1
]}

Higuchi, Keiko ^{[1
]}

Thasana, Nopporn ^{[2
]}

Yamada, Hitomi ^{[1
]}

Nishikawa, Toshio ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan

[2] Chulabhorn Res Inst, Med Chem Lab, Bangkok 10210, Thailand

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

LIPID DROPLET SYNTHESIS; ORGANOSTANNANES; INHIBITOR;

D O I：

10.1021/ol202895u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two possible diastereomers of the indole moiety of sespendole were synthesized from 3-hydroxy-4-nitrobenzaldehyde in a highly stereoselective manner. Comparison of H-1 and C-13 NMR spectra of the two synthetic materials with those sespendole leads us to propose that the relative stereochemistry of the epoxyalcohol is syn.

引用

页码：114 / 117

页数：4

共 22 条

[11] A fully synthetic route to the neurotrophic illicinones: Syntheses of tricycloillicinone and bicycloillicinone aldehyde [J].

Pettus, TRR ;

Inoue, M ;

Chen, XT ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6160-6168

[12] PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES - A SHORT SYNTHESIS OF PLERAPLYSILLIN-1 [J].

SCOTT, WJ ;

CRISP, GT ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4630-4632

[13] PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES - SYNTHETIC AND MECHANISTIC STUDIES [J].

SCOTT, WJ ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3033-3040

[14] Indole diterpene synthetic studies:: Development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B [J].

Smith, Amos B., III ;

Kurti, Laszlo ;

Davulcu, Akin H. ;

Cho, Young Shin ;

Ohmoto, Kazuyuki .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4611-4620

[15] Indole diterpene synthetic studies.: Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D [J].

Smith, Amos B., III ;

Davulcu, Akin H. ;

Cho, Young Shin ;

Ohmoto, Kazuyuki ;

Kurti, Laszlo ;

Ishiyama, Haruaki .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4596-4610

[16] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES [J].

SONOGASHIRA, K ;

TOHDA, Y ;

HAGIHARA, N .

TETRAHEDRON LETTERS, 1975, (50) :4467-4470

[17] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES [J].

STILLE, JK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :508-523

[18] Synthetic Study on Sespendole, an Indole Sesquiterpene Alkaloid: Stereocontrolled Synthesis of the Sesquiterpene Segment Bearing All Requisite Stereogenic Centers [J].

Sugino, Kumi ;

Nakazaki, Atsuo ;

Isobe, Minoru ;

Nishikawa, Toshio .

SYNLETT, 2011, (05) :647-650

[19] Sespendole, a new inhibitor of lipid droplet synthesis in macrophages, produced by Pseudobotrytis terrestris FKA-25 [J].

Uchida, R ;

Kim, YP ;

Namatame, I ;

Tomoda, H ;

Omura, S .

JOURNAL OF ANTIBIOTICS, 2006, 59 (02) :93-97

[20] Structure elucidation of fungal sespendole, an inhibitor of lipid droplet synthesis in macrophages [J].

Uchida, Ryuji ;

Kim, Yong-Pil ;

Nagamitsu, Tohru ;

Tomoda, Hiroshi ;

Omura, Satoshi .

JOURNAL OF ANTIBIOTICS, 2006, 59 (06) :338-344

← 1 2 3 →