Progress in the Chemistry of Organic Natural Products

by Herz, W.; Kirby, G. W.; Falk, H.

• ISBN13: 9783211837832
• ISBN10: 3211837833
• Format: Hardcover
• Copyright: 2003-02-01
• Publisher: Springer Nature

Summary

The volumes of this classic series, now referred to simply as "Zechmeister''‚¬Â¥ after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics related to the origin, distribution, chemistry, synthesis, biochemistry, function or use of various classes of naturally occurring substances ranging from small molecules to biopolymers. Each contribution is written by a recognized authority in his field and provides a comprehensive and up-to-date review of the topic in question. Addressed to biologists, technologists, and chemists alike, the series can be used by the expert as a source of information and literature citations and by the non-expert as a means of orientation in a rapidly developing discipline.

Table of Contents

List of Contributors	x
Natural Products Derived from Naphthalenoid Precursors by Oxidative Dimerization
K. Krohn
Introduction	1	(2)
Isolation and Structure Elucidation	3	(26)
Spirobisnaphthalenes with Two Oxygen Bridges	3	(18)
Spirobisnaphthalenes with Three Oxygen Bridges (Preussomerins)	21	(4)
Spirobisnaphthalenes with Two Oxygen Bridges and One C-C Bridge (Spiroxins)	25	(1)
Determination of Relative and Absolute Stereochemistry	26	(3)
Biological Activity	29	(1)
Biosynthesis	30	(4)
Synthesis	34	(17)
Biomimetic Type Approach	34	(5)
Spiroketalization Approach	39	(7)
Acknowledgements	46	(1)
References	46	(5)
Prokaryotic Glycoproteins
P. Messner
C. Schaffer
Introduction	51	(2)
S-Layer Glycoproteins	53	(29)
Uniqueness of S-Layer Glycoproteins	53	(11)
From Chemical Composition to Structural Concept	64	(11)
Biosynthesis	75	(3)
Molecular Biological Insights	78	(2)
Perspectives	80	(2)
Non-S-Layer Glycoproteins	82	(22)
Intracellular Glycoproteins	83	(1)
Membrane-Associated Glycoproteins	84	(4)
Surface-Associated Glycoproteins	88	(4)
Extracellular Glycoproteins	92	(5)
``Cellular'' Glycoproteins	97	(4)
Synthetic Glycopeptides and Glycoproteins	101	(3)
Conclusions	104	(24)
Acknowledgements	105	(1)
References	105	(23)
Carbazole Alkaloids IV
D. P. Chakraborty
S. Roy
Introduction	128	(4)
Nomenclature	129	(1)
Occurrence	129	(3)
Methods of Structure Elucidation	132	(36)
Physical Methods	132	(1)
Ultraviolet Absorption Spectra	133	(1)
IR Spectra	133	(1)
NMR Spectra	133	(10)
Mass Spectra	143	(1)
X-ray Crystallography	144	(1)
Chemical Methods	145	(1)
Synthesis	145	(1)
Synthesis from Monocyclic Systems	145	(9)
Synthesis from Bicyclic Systems	154	(9)
Synthesis from Tricyclic Systems	163	(2)
Synthesis of Carbazoles by Electrocyclisation	165	(1)
Synthesis by Photolytic Methods	166	(2)
Biogenesis of Carbazole Alkaloids	168	(2)
Biological and Therapeutic Properties of Carbazoles and Carbazole Alkaloids	170	(5)
Chemistry of Carbazole Alkaloids	175	(56)
Alkaloids from Higher Plants	175	(1)
C13-Alkaloids	175	(1)
9-Carboethoxy-3-methylcarbazole	175	(1)
Clausenol	175	(1)
Clausenine	176	(1)
9-Formyl-3-methylcarbazole	176	(1)
Murrayaline B	176	(1)
2-Methyl-7-hydroxycarbazole or 2-Hydroxy-7-methylcarbazole	177	(1)
N-Methoxy-3-hydroxymethylcarbazole	177	(1)
3-Formyl-7-hydroxycarbazole	177	(1)
O-Methylmukonal	178	(1)
3-Formyl-6-methoxycarbazole	178	(1)
7-Methoxymukonal	178	(1)
Clausenal	179	(1)
6-Methoxymurrayanine	179	(1)
7-Methoxy-O-methylmukonal	180	(1)
Murrayaline C	180	(1)
Carbazole-3-carboxylic Acid	180	(1)
3-Carbomethoxycarbazole	180	(1)
Clauszoline C	181	(1)
3-Carbomethoxy-6-methoxycarbazole	181	(1)
Clauszoline I	181	(1)
Clauszoline J	182	(1)
Clauszoline K	182	(1)
Clauszoline L	183	(1)
Clauszoline M	183	(1)
C18-Alkaloids	183	(1)
Clauszoline B	183	(1)
Clauszoline D	184	(1)
Euchrestine A	184	(1)
Eustofoline D	185	(1)
Furostifoline	185	(1)
Glycomaurine	185	(1)
Glycomaurol	186	(1)
7-Methoxyheptaphylline	186	(1)
7-Methoxymurrayacine	187	(1)
Murrayamine A	187	(1)
Pyrayafoline B	188	(1)
Pyrayafoline C	188	(1)
Mukoenine A	189	(1)
Mukoenine C	189	(1)
Murrayaquinone E	189	(1)
Clauszoline H	190	(1)
C23-Alkaloids	190	(1)
Clauszoline A	190	(1)
Clauszoline F	191	(1)
Euchrestine B	191	(1)
Euchrestine C	192	(1)
Euchrestine D	192	(1)
Euchrestine E	193	(1)
Eustifoline B	193	(1)
Eustifoline C	193	(1)
Isomahanine	194	(1)
(+)-Mahanine	194	(1)
Murrayaline D	195	(1)
Murrayamine B	195	(1)
Murrayamine C	196	(1)
Murrayanol	196	(1)
Pyrayafoline D	197	(1)
Murrayaquinone C	197	(1)
Murrayaquinone D	197	(1)
Pyrayafoline E	198	(1)
Mukoenine B	198	(1)
Dimeric Carbazole Alkaloids from Higher Plants	199	(1)
C26-Alkaloids	199	(1)
Indole Dimer	199	(1)
Bis-2-hydroxy-3-methylcarbazole	200	(1)
Bismurrayaquinone A	200	(1)
Chrestifoline A	201	(1)
Cherestifoline D	201	(1)
Murrastifoline A	202	(1)
Murrastifoline B	202	(1)
Murrastifoline F	203	(1)
C31-Alkaloids	203	(1)
Chrestifoline B	203	(1)
Murrafoline G	204	(1)
Murrastifoline D	204	(1)
Murrastifoline E	205	(1)
C36-Alkaloids	206	(1)
Chrestifoline C	206	(1)
Murrafoline H	206	(1)
Murrastifoline C	207	(1)
Bis-7-hydroxygirinimbine A	208	(1)
Bis-7-hydroxygirinimbine B	208	(1)
Murranimbine	208	(2)
C46-Alkaloids	210	(1)
Bismahanine	210	(1)
Bismurrayafoline C	210	(1)
Bismurrayafoline D	211	(1)
Alkaloids from Lower Plants	211	(1)
Alkaloids from Microbial Sources	212	(1)
Alkaloids Built on a Carbazole Skeleton	212	(1)
Aflavazole	212	(1)
Carazostatin	213	(1)
Carquinostatin A	213	(1)
Indolocarbazoles	214	(1)
Alkaloids Built on an Indolocarbazole Skeleton (Two Nitrogens)	214	(1)
Antitumor Compound AT 2433 A1	214	(1)
Antitumor Compound AT 2433 A2	215	(1)
Antitumor Compound AT 2433 B1	215	(1)
Antitumor Compound AT 2433 B2	215	(1)
Arcyriaflavin B	216	(1)
Arcyriaflavin C	216	(1)
Protein Kinase C Inhibitor K-252a	217	(1)
Protein Kinase C Inhibitor K-252b	217	(1)
Protein Kinase C Inhibitor K-252c	218	(1)
Protein Kinase C Inhibitor K-252d	218	(1)
Rebeccamycin	219	(1)
Staurosporine	219	(1)
Tan 1030 A	220	(1)
Tan 999	221	(1)
UCN-01	222	(1)
Alkaloids from Marine Sources	222	(1)
1-Methylcarbazole	222	(1)
1-Acetylcarbazole	223	(1)
Aldose Reductase Inhibitors	223	(1)
References	224	(7)
Author Index	231	(14)
Subject Index	245