http://www.rsc.org/suppdata/CC/b9/b901940e/b901940e.pdf

Bicyclic-guanidines, -guanidinates and -guanidinium salts: wide ranging applications from a simple family of molecules

The simple β-carboline alkaloids

Reserpine: A Challenge for Total Synthesis of Natural Products

Previous chapters in this series by Warren appeared in 1955 (310) and 1966 (311). Since then an authoritative book by Bull, Culvenor, and Dick, on the chemistry and pharmacology of pyrrolizidine alkaloids has been published (60). Comprehensive reviews on the alkaloids (312), their chemotaxonomic significance (77), and general pyrrolizidine chemistry (243) are available. A series of Annual Reports including pyrrolizidine alkaloids was introduced in 1971 (245). The present review follows the format of previous articles in this series and covers the literature up to early 1981.

The pyrrolizidine alkaloids.

Natural guanidine derivatives

In a preliminary note [1] we established the plane structure of the prosopine 1,2-hydroxymethyl 3-hydroxy 6-dodecyl 11°-hydroxypiperidine and the prosopinine 8, 2-hydroxymethyl 3-hydroxy 6-dodecyl 10°-keto piperidine, alkaloids isolated from Prosopis africana (Guill & Perr) Taub.



This paper contains the study of the reduction products of the pyrrolidine 18b and the establishment of the relative and absolute configurations of these two alkaloids. The experimental part involves the details for the determination of these structures and also the extraction method of these two alkaloids as well as the new alkaloids: prosophylline, prosafrine and the prosafrinine isolated from leaves of P. africana and isoprosopinines A and B extracted from roots and stem bark of the same plant. The establishment of the structure of the new five alkaloids is the subject of the next paper.

Alcaloïdes Pipéridiniques II. Structures de la Prosopine et de la Prosopinine, Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub. [1]

Alcaloïdes indoliques—CII : Deux nouveaux types d'alcaloïdes indoliques l'ibophyllidine, dérivé du nor-21(+)pandolane et l'iboxyphylline dérivé de l'abeo-21(20→19) (+)pandolane, retirés des feuilles de tabernanthe iboga baillon et de t. subsessilis stapf

The structures of five new alkaloids have been established: the isoprosopinines A and B, 1 and 2 are homogeneous mixture: isoprosopinine A is (2R, 3S, 6R) 2-hydroxymethyl 3-hydroxy 6-dodecyl 7°-keto piperidine and isoprosopinine B is (2R, 3S, 6R) 2-hydroxymethyl 3-hydroxy 6-dodecyl 8°-keto piperidine.



Prosophylline 4 is d 2-hydroxymethyl 3-hydroxyl 6-dodecyl 10°-keto piperidine, prosafrine 9 is (2R, 3R, 6S) 2-methyl 3-hydroxy 6-dodecyl 10°-hydroxy piperidine and prosafrinine 11, is (2R, 3R, 6S) 2-methyl 3-hydroxy 6-dodecyl 10°-keto piperidine.

Alcaloïdes Pipéridiniques III. Nouveaux Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub.: Isoprosopinines A et B, Prosophylline, Prosafrine Et Prosafrinine [1]

Robert Goutarel

Papers

Alcaloïdes Pipéridiniques II. Structures de la Prosopine et de la Prosopinine, Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub. [1]

Alcaloïdes indoliques—CII : Deux nouveaux types d'alcaloïdes indoliques l'ibophyllidine, dérivé du nor-21(+)pandolane et l'iboxyphylline dérivé de l'abeo-21(20→19) (+)pandolane, retirés des feuilles de tabernanthe iboga baillon et de t. subsessilis stapf

Alcaloïdes Pipéridiniques III. Nouveaux Alcaloïdes du Prosopis Africana (Guill. et Perr.) Taub.: Isoprosopinines A et B, Prosophylline, Prosafrine Et Prosafrinine [1]

Alcaloïdes des Homalium: Structure de l'homaline, de l'hopromine, de l'hoprominol et de l'hopromalinol

Alchornéine, isoalchornéine et alchornéinone, produits isolés de l'Alchornea floribunda Muell. Arg.