Diastereoselective synthesis of (+)-pseudohygroline via proline-catalyzed alpha-hydroxylation

Diastereoselective synthesis of (+)-pseudohygroline via proline-catalyzed alpha-hydroxylation

A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-alpha-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical...

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Bibliographic Details
Published in:Natural product communications Vol. 9; no. 5; p. 633
Main Authors: Anusha, Bheemreddy, Reddy, Ummareddy V Subba, Reddy, Basireddy V Subba, Reddy, Cirandur Suresh
Format: Journal Article
Language:English
Published: United States 01-05-2014
Subjects:
Catalysis
Hydroxylation
Proline - metabolism
Pyrrolidines - metabolism
Stereoisomerism
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Summary:A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-alpha-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical proof of the absolute stereochemistry of biosynthetically important (+)-hygroline (2) and (+)-hygrine (3).
ISSN:1934-578X
DOI:10.1177/1934578X1400900510