Biomimetic Syntheses of the Flindersial Alkaloids

被引：13

作者：

Vallakati, Ravikrishna ^{[1
]}

May, Jeremy A. ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

SYNLETT | 2012年 / 18期

关键词：

natural products; alkaloids; biomimetic synthesis; tandem reactions; regioselectivity; BORRERIA-VERTICILLATA; NEW-CALEDONIA; ISOBORREVERINE; BORREVERINE; FOURNIERI; PLANTS;

D O I：

10.1055/s-0032-1317416

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The flindersial alkaloids have a potentially novel mechanism for antimalarial activity. The recently disclosed flinderoles were postulated to be derived through dimerization of the natural product borrerine in a manner similar to their structural isomers, the borreverines. Recent work by the authors has shown that the flindersial alkaloids share a common biosynthetic origin to that of borrerine. The application of this insight has resulted in the synthesis of naturally occurring flindersial alkaloids with controlled formation of the structural isomer. Only three synthetic steps from tryptamine are needed for any of the natural products.

引用

页码：2577 / 2581

页数：5

共 14 条

[1] SPERMACOCEINE, A BIS-INDOLE ALKALOID FROM BORRERIA-VERTICILLATA
BALDE, AM
PIETERS, LA
GERGELY, A
WRAY, V
CLAEYS, M
VLIETINCK, AJ
[J]. PHYTOCHEMISTRY, 1991, 30 (03) : 997 - 1000
[2] Biomimetic Total Syntheses of Flinderoles B and C
Dethe, Dattatraya H.
Erande, Rohan D.
Ranjan, Alok
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (09) : 2864 - 2867
[3] Antimalarial Activity of Natural Product Extracts from Papua New Guinean and Australian Plants against Plasmodium falciparum
Fernandez, Liza S.
Jobling, Michael F.
Andrews, Katherine T.
Avery, Vicky M.
[J]. PHYTOTHERAPY RESEARCH, 2008, 22 (10) : 1409 - 1412
[4] Antiparasitic activity of alkaloids from plant species of Papua New Guinea and Australia
Fernandez, Liza S.
Sykes, Melissa L.
Andrews, Katherine T.
Avery, Vicky M.
[J]. INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2010, 36 (03) : 275 - 279
[5] Flinderoles A-C: Antimalarial Bis-indole Alkaloids from Flindersia Species
Fernandez, Liza S.
Buchanan, Malcolm S.
Carroll, Anthony R.
Feng, Yun Jiang
Quinn, Ronald J.
Avery, Vicky M.
[J]. ORGANIC LETTERS, 2009, 11 (02) : 329 - 332
[6] Pousset J.L., 1977, J CHEM SOC CHEM COMM, P261
[7] BORRERINE - NEW ALKALOID ISOLATED FROM BORRERIA-VERTICILLATA
POUSSET, JL
KERHARO, J
MAYNART, G
MONSEUR, X
CAVE, A
GOUTAREL, R
[J]. PHYTOCHEMISTRY, 1973, 12 (09) : 2308 - 2310
[8] STRUCTURE OF AURICULARINE, A BIS-INDOLE ALKALOID FROM HEDYOTIS-AURICULARIA
PURUSHOTHAMAN, KK
SARADA, A
[J]. PHYTOCHEMISTRY, 1981, 20 (02) : 351 - 352
[9] TILLEQUIN F, 1979, LLOYDIA, V42, P92
[10] BIOMIMETIC SYNTHESIS OF BORREVERINE AND ISOBORREVERINE
TILLEQUIN, F
KOCH, M
POUSSET, JL
CAVE, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (19) : 826 - 828

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