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A Short Synthesis of a Thromboxane B 2 Key Intermediate from (R) ‐2,3‐Isopropylideneglyceraldehyde. γ‐Lactones as Templates for Chemoselective cis ‐Annulation of Pyranosides
Author(s) -
Mulzer Johann,
Graske KlausDieter,
Shanyoor Mazin
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950482
Subject(s) - chemistry , annulation , lactone , stereochemistry , bicyclic molecule , acetal , diol , organic chemistry , catalysis
A six‐step synthesis of the bicyclic lactone pyranoside 1 , which has served as a key intermediate in numerous syntheses of thromboxane B 2 , from (R) ‐2,3‐isopropylideneglyceraldehyde is described. In contrast to the previous syntheses of 1 the lactone part is prepared first and acts as a template in the annulation of the hemiketal unit. Further aspects of interest are the Felkin‐Anh‐controlled addition of vinyl cuprates to the acrylic ester 16 and the considerable rate difference in the formation of the γ‐lactones 13, 14, 19 , and 21 from the corresponding hydroxy acids.