Remarkable Switch of Regioselectivity in Diels-Alder Reaction: Divergent Total Synthesis of Borreverine, Caulindoles, and Flinderoles

被引：29

作者：

Dethe, Dattatraya H. ^{[1
]}

Erande, Rohan D. ^{[1
]}

Dherange, Balu D. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 10期

关键词：

BORRERIA-VERTICILLATA; FLINDERSIAL ALKALOIDS; BIOMIMETIC SYNTHESIS; DIMERIC COUMARIN; ISOBORREVERINE; CONSTITUENTS; PLANTS;

D O I：

10.1021/ol501078d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products.

引用

页码：2764 / 2767

页数：4

共 30 条

[1]

Achenbach H., 1995, PHYTOCHEMISTRY, P40

[2] SPERMACOCEINE, A BIS-INDOLE ALKALOID FROM BORRERIA-VERTICILLATA [J].

BALDE, AM ;

PIETERS, LA ;

GERGELY, A ;

WRAY, V ;

CLAEYS, M ;

VLIETINCK, AJ .

PHYTOCHEMISTRY, 1991, 30 (03) :997-1000

[3] THE CONSTITUENTS OF PHEBALIUM-NUDUM HOOK .1. THE BARK [J].

BRIGGS, LH ;

CAMBIE, RC .

TETRAHEDRON, 1958, 2 (3-4) :256-270

[4] Biomimetic Total Syntheses of Borreverine and Flinderole Alkaloids [J].

Dethe, Dattatraya H. ;

Erande, Rohan D. ;

Ranjan, Alok .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10106-10120

[5] Biomimetic Total Syntheses of Flinderoles B and C [J].

Dethe, Dattatraya H. ;

Erande, Rohan D. ;

Ranjan, Alok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (09) :2864-2867

[6] CONSTITUENTS OF THAMNOSMA NONTANA TORR AND FREM [J].

DREYER, DL .

TETRAHEDRON, 1966, 22 (08) :2923-&

[7] Antimalarial Activity of Natural Product Extracts from Papua New Guinean and Australian Plants against Plasmodium falciparum [J].

Fernandez, Liza S. ;

Jobling, Michael F. ;

Andrews, Katherine T. ;

Avery, Vicky M. .

PHYTOTHERAPY RESEARCH, 2008, 22 (10) :1409-1412

[8] Flinderoles A-C: Antimalarial Bis-indole Alkaloids from Flindersia Species [J].

Fernandez, Liza S. ;

Buchanan, Malcolm S. ;

Carroll, Anthony R. ;

Feng, Yun Jiang ;

Quinn, Ronald J. ;

Avery, Vicky M. .

ORGANIC LETTERS, 2009, 11 (02) :329-332

[9]

HOCQUEMILLER R, 1978, Plantes Medicinales et Phytotherapie, V12, P230

[10] ALKALOIDS FROM ANNONACEAE .49. ALKALOIDS ISOLONA-HEXALOBA, ISOLONA-ZENKERI AND ISOLONA-PILOSA [J].

HOCQUEMILLER, R ;

CABALION, P ;

FOURNET, A ;

CAVE, A .

PLANTA MEDICA, 1984, 50 (01) :23-25

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