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Asymmetric Synthesis of ( R,S )‐Dehydroiridodial, ( R,S )‐Dehydroiridodiol and Analogues
Author(s) -
Enders Dieter,
Kaiser Anja
Publication year - 1997
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.199719970308
Subject(s) - chemistry , enantiomer , michael reaction , stereochemistry , organic chemistry , catalysis
The synthesis of ( R,S )‐(–)‐dehydroiridodiol(dial) [( R,S )‐ 6b ], isolated from the plant Actinidia polygama Miq., and its analogues, in high diastereo‐ and enantiomeric purity (ee ⩾ 96%) is described. Key steps of the synthesis are the Michael addition of metallated SAMP hydrazones [( S )‐ 1 ] to the 2‐cyclopentenecarboxylate 2 and subsequent conversion to the 5‐substituted 2‐methylcyclopentenecarboxylates 5 .