Synthesis of the putative structures of homopumiliotoxins 235C and 233F

被引：9

作者：

Armstrong, P ^{[1
]}

Feutren, S ^{[1
]}

McAlonan, H ^{[1
]}

O'Mahony, G ^{[1
]}

Stevenson, PJ ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期

关键词：

homopumiliotoxin alkaloids; Heck reaction;

D O I：

10.1016/j.tetlet.2003.12.126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1627 / 1630

页数：4

共 31 条

[1] [Anonymous], 1993, ALKALOIDS CHEM PHARM
[2] HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-ALLOPUMILIOTOXIN-339A
AOYAGI, S
WANG, TC
KIBAYASHI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10653 - 10654
[3] Total synthesis of (+)-homopumiliotoxin 223G
Aoyagi, S
Hasegawa, Y
Hirashima, S
Kibayashi, C
[J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2149 - 2152
[4] DIFFERENTIAL INHIBITION OF AMINOPEPTIDASE-A AND AMINOPEPTIDASE-N BY NEW BETA-AMINO THIOLS
CHAUVEL, EN
LLORENSCORTES, C
CORIC, P
WILK, S
ROQUES, BP
FOURNIEZALUSKI, MC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (18) : 2950 - 2957
[5] Ernest Guenther award in chemistry of natural products. Amphibian skin: A remarkable source of biologically active arthropod alkaloids
Daly, JW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (04) : 445 - 452
[6] TOXICITY OF PANAMANIAN POISON FROGS (DENDROBATES) - SOME BIOLOGICAL AND CHEMICAL ASPECTS
DALY, JW
MYERS, CW
[J]. SCIENCE, 1967, 156 (3777) : 970 - &
[7] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[8] Palladium catalysed formal 6-endo-trig approaches to pumiliotoxin alkaloids:: interception of the elusive cyclopropyl intermediate
Feutren, S
McAlonan, H
Montgomery, D
Stevenson, PJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07): : 1129 - 1137
[9] Total syntheses of pumiliotoxin A and allopumiliotoxin alkaloids. Interplay of pharmacologically active natural products and new synthetic methods and strategies
Franklin, AS
Overman, LE
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 505 - 522
[10] ALKALOIDS IN MADAGASCAN FROGS (MANTELLA) - PUMILIOTOXINS, INDOLIZIDINES, QUINOLIZIDINES, AND PYRROLIZIDINES
GARRAFFO, HM
CACERES, J
DALY, JW
SPANDE, TF
ANDRIAMAHARAVO, NR
ANDRIANTSIFERANA, M
[J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07): : 1016 - 1038

← 1 2 3 4 →