Chiron approach to (−)-deoxocuscohygrine

A facile chiron approach to C2-symmetrical (−)-deoxocuscohygrine is described by using cross metathesis as the key step.

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(S)-tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylateC10H19NO3[α]D25=-39.75 (c 1.2, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (S)

(S)-tert-Butyl 2-vinylpyrroline-1-carboxylateC11H19NO2[α]D25=-11.5 (c 1.0, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (S)

(S)-tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylateC11H21NO3[α]D25=-10.7 (c 1.4, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (S)

(S)-tert-Butyl 2-allylpyrrolidine-1-carboxylateC12H21NO2[α]D25=-27.1 (c 1.1, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (S)

(2S,2′S)-tert-Butyl 2,2′-((E)-but-2-ene-1,4-diyl)dipyrrolidine-1-carboxylateC22H38N2O4[α]D25=-42.2 (c 1.1, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (2S,2′S)

(2S,2′S)-tert-Butyl 2,2′-((E)-ethene-1,2-diyl)dipyrrolidine-1-carboxylateC20H34N2O4[α]D25=-51.4 (c 0.4, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (2S,2′S)

(2R,2′R)-tert-Butyl 2,2′-(butane-1,4-diyl)dipyrrolidine-1-carboxylateC21H38N2O4[α]D25=-28.85 (c 1.1, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (2R,2′R)

1,4-Bis((R)-1-methylpyrrolidin-2-yl)butaneC13H26N2[α]D25=-62.5 (c 0.4, CHCl3)Source of chirality: l-(−)-prolineAbsolute configuration: (R,R)