Progress in the Chemistry of Organic Natural Products

by Zechmeister, L.; Herz, W.; Falk, H.; Kirby, G. W.; Moore, R. E.

• ISBN13: 9783211832646
• ISBN10: 3211832645
• Format: Hardcover
• Copyright: 1999-07-01
• Publisher: Springer Verlag

Summary

Diese bekannte Reihe behandelt in Beiträgen bedeutender Autoren den jeweils letzten Stand des Wissens über die verschiedenen Klassen der in der Natur auftretenden Verbindungen. Es werden behandelt: Vorkommen, Reindarstellung, Struktur, chemische Eigenschaften, Synthese, Biogenese und Funktion.

Table of Contents

List of Contributors	vii
Secondary Metabolites and the Control of Some Blue Stain and Decay Fungi	1	(20)
W. A. Ayer
L. S. Trifonov
Introduction	1	(2)
Blue Stain Fungi	3	(6)
Blue Stain on Conifers	3	(1)
Blue Stain on Broadleaf Trees	4	(5)
Decay Causing Fungi	9	(8)
Decay on Conifers	9	(2)
Decay on Broadleaf Trees	11	(6)
The Black Gall Effect	17	(4)
Acknowledgements	17	(1)
References	17	(4)
Condensed Tannins	21	(48)
D. Ferreira
E. V. Brandt
J. Coetzee
E. Malan
Introduction	22	(1)
Formation of the Interflavanyl Bond in Oligomeric Proanthocyanidins	22	(19)
Synthesis of the First Profisetinidins with Epifisetinidol Constituent Units	25	(4)
Synthesis of Procyanidins under Neutral Conditions	29	(2)
Synthesis of Ether-Linked Proteracacinidins	31	(5)
Miscellaneous	36	(3)
Formation of the Ether Linkage in A-Type Proanthocyanidins	39	(2)
Cleavage of the Interflavanyl Bond in Oligomeric Proanthocyanidins	41	(8)
B-Type Proanthocyanidins	41	(6)
A-Type Proanthocyanidins	47	(2)
Rearrangement of the Pyran Heterocycle of Oligomeric Proanthocyanidins	49	(7)
Introduction	49	(1)
Base-Catalyzed Pyran Ring Rearrangement of Oligomeric Proanthocyanidins	50	(4)
Acid-Catalyzed Rearrangement of Procyanidins and Prodelphinidins under Conditions of Thiolytic Cleavage	54	(2)
Conformational Analysis of Dimeric Proanthocyanidins	56	(3)
Conclusion	59	(10)
Acknowledgements	59	(1)
References	59	(10)
Constituents of Lactarius (Mushrooms)	69	(104)
W. M. Daniewski
G. Vidari
Introduction	70	(3)
Sesquiterpenes Isolated from Lactarius	73	(12)
Farnesane Sesquiterpenes	75	(2)
Caryophyllane Sesquiterpenes	77	(1)
Drimane Sesquiterpenes	78	(3)
Guaiane Sesquiterpenes	81	(3)
Protoilludane Sesquiterpenes	84	(1)
Introduction to Parts 6 and 7 - Velutinal Esters and Related Sesquiterpenes	85	(43)
Marasmane, Isomarasmane, and Normarasmane Sesquiterpenes	87	(2)
Heterocyclic Marasmane Sesquiterpenes	89	(3)
Glutinopallane Sesquiterpenes	92	(1)
Isolactarane Sesquiterpenes	93	(2)
Lactarane Sesquiterpenes	95	(4)
5-Lactaranolide Sesquiterpenes	99	(8)
5-Lactaranolide Derivatives	107	(1)
Rearranged 5-Lactaranolide Sesquiterpenes	107	(1)
8,9-Seco-5-lactaranolide Sesquiterpenes and Derivatives	108	(1)
Norlactarane Sesquiterpenes	109	(2)
13-Lactaranolide Sesquiterpenes	111	(4)
13-Lactaranolide Derivatives	115	(1)
Furanolactarane Sesquiterpenes	115	(3)
8,9-Secofuranolactarane Sesquiterpenes	118	(2)
Rearranged Furanolactarane Sesquiterpenes	120	(1)
Dibenzonaphthyridinone Alkaloids	120	(3)
Prenylated Phenols, Benzofurans, Chromanes	123	(5)
Miscellaneous Compounds	128	(1)
Chemistry of Sesquiterpenes of Lactarius	128	(45)
Interconversions and Reactions	129	(10)
Total Syntheses	139	(18)
Biological Properties of Metabolites of Lactarius Origin	157	(4)
References	161	(12)
Author Index	173	(6)
Subject Index	179