Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal

Ana Sirvent; Sandra Hernández-Ibáñez; Miguel Yus; Francisco Foubelo

doi:10.1055/s-0037-1610763

Synthesis, Table of Contents

Synthesis 2021; 53(10): 1749-1759
DOI: 10.1055/s-0037-1610763

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Pyrrolidine and Indolizidine Alkaloids from Chiral N-tert-Butanesulfinyl Imines Derived from 4-Halobutanal

Ana Sirvent

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^bInstituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^cCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

,

Sandra Hernández-Ibáñez

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^bInstituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^cCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

,

Miguel Yus∗

^cCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

,

Francisco Foubelo∗

^aDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^bInstituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

^cCentro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

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Abstract

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Dedicated to Professor Joaquín Plumet on the occasion of his 75^th birthday

Abstract

An efficient stereocontrolled preparation of 2-substituted pyrrolidines and 5-substituted indolizidin-7-ones, by using chiral N-tert-butanesulfinyl imines derived from 4-halobutanal as starting materials, is detailed. Addition of Grignard reagents and a decarboxylative Mannich reaction with β-keto acids involving these chiral imines proceeded with high diastereoselectivity. The synthesis of the pyrrolidinic alkaloids (–)-bgugaine, (+)-villatamine B, (–)-norhygrine, trans-dendrochrysanine, and (–)-ruspolinone demonstrated the utility of this methodology.

Key words

chiral sulfinyl imines - diastereoselective additions - decarboxylative Mannich reaction - bgugaine - villatamine - norhygrine - trans-dendrochrysanine - ruspolinone

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References

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