Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progres dans l

Substances belonging to this group of organic compounds are wi,lely distributed in Nature, being found in plants, both higher and lower fungi and, upto the present time, in one animal source, sheep wool-fat. For a long­ time no real differentiation was po

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EDITED BY

L. ZECHMEISTER CALIFORNIA INSTITUTE OF TECHNOLOGY. PASADENA

ZWOLFTER BAND TWELFTH VOLUME DOUZLEME VOLUME VERPASSER

AUTHORS

AUTEURS

O. W. BEADLE· A. I. HAAOEN·SMIT . T. O. HALSALL . F. T. HAXO E. R. H. IONES . R. MICHEL . J. ROCHE . K. SLOTTA . A. R. THOMPSON E. O. P. THOMPSON· R. TSCHESCHE . F. L. WARREN MIT IS ABBILDUNOEN

WlTH IS ILLUSTRATIONS

AVEC IS ILLUSTRATIONS

WI EN· S P R IN G E R.V E R L A G·1955

ALLE RECHTE, INSBESONDERE DAS DER OBERSETZUNG IN FREMDE SPRACHEN, VORBEHALTEN

Softcover reprint of the hardcover 1st edition 1987

ISBN 978-3-7091-7168-4 ISBN 978-3-7091-7166-0 (eBook) DOI 10.1007/978-3-7091-7166-0

Inhaltsverzeichnis. Contents. - Table des mati(~res. Sesquiterpenes and Diterpenes. By A.

J.

HAAGEN-SMIT, Canfornia Institute of Technology. Pasadena. California ...................... .

Introduction ......................................................... . I. Sesquiterpenes.................................................... I.

2.

3. 4. 5. 6. 7.

8. 9. 10. II.

12.

Acyclic Sesquiterpenes ........................................ Bisabolene and Cadinene Type SesquitellJenes.................... Eudesmol Type Sesquiterpenes ..................•.............. Elemol ....................................................... Eremophilone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Iresin ........................................................ Azulene Type Sesquiterpenes ., ..... " . . . . . . . . . . . . .. . . . ... . .. . . . Synthesis and Properties of Azulenes............................ Longifolene ... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Caryophyllene................................................. p-Caryophyllene Alcohol........................................ Humulene .................................................... Cedrene ......................................................

3 3 3 6 8 8 9 10

12

14 16 17

18 18

II. Diterpenes........................................................ I. Structure..................................................... 2. Stereochemistry of the Diterpenes ..............................

23

III. The Biogenesis of Sesqui- and Diterpenes........................... Biogenesis and !'i-Terminal Sequences .......................................... a) Dinitrofluorobenzene Method ................................. b) Isothiocyanate Method . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. c) Other Methods. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..

303 303 j08 3I 1

2.

C-Terminal Sequences ........................................... a) Carboxypeptidase Method. .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. b) Reduction Methods ................................ . . . . . . . . .. c) Other Methods ..............................................

315 3I 5 j19 319

3. Conclusion......................................... . . . . . . .