Frank S. Ungemach scite author profile

The title diol (6a) has been shown to be a metabolite of Rhizoctonia leguminicola, the fungus that produces two toxic indolizidine alkaloids, swainsonine (1) and slaframine (2). The structure of 6a was established spectroscopically and confirmed by synthesis of both C-8a epimers 6a and 7a. The absolute configuration was inferred from the efficient reutilization of the isolated 6a to form 1. Diol 7a could not be detected among the products of fermentation. It is noteworthy that 6a is probably an intermediate in the biosynthesis of swainsonine although it differs from the alkaloid in being epimeric at the 8a position.

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Biosynthesis of swainsonine in Rhizoctonia leguminicola. Epimerization at the ring fusion

Schneider¹,

Ungemach²,

Broquist³

et al. 1982

J. Am. Chem. Soc.

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Stereospecific synthesis of -1,3-disubstituted-1,2,3,4-tetrahydro β-carbolines

Ungemach

DIPIERRO

Weber

et al. 1979

Tetrahedron Letters

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ChemInform Abstract: STEREOSPECIFIC SYNTHESIS OF TRANS‐1,3‐DISUBSTITUTED‐1,2,3,4‐TETRAHYDRO β‐CARBOLINES

Ungemach¹,

DIPIERRO²,

Weber³

et al. 1979

Chemischer Informationsdienst

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Frank S. Ungemach

General method for the assignment of stereochemistry of 1,3-disubstituted 1,2,3,4-tetrahydro-.beta.-carbolines by carbon-13 spectroscopy

(1S,2R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizine (swainsonine), an α-mannosidase inhibitor from Rhizoctonia leguminicola

Study of the Pictet-Spengler reaction in aprotic media: synthesis of the .beta.-galactosidase inhibitor, pyridindolol

Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines

(1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine

Biosynthesis of swainsonine in Rhizoctonia leguminicola. Epimerization at the ring fusion

Stereospecific synthesis of -1,3-disubstituted-1,2,3,4-tetrahydro β-carbolines

ChemInform Abstract: STEREOSPECIFIC SYNTHESIS OF TRANS‐1,3‐DISUBSTITUTED‐1,2,3,4‐TETRAHYDRO β‐CARBOLINES

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