ISSN:
0947-3440
Keywords:
Michael addition
;
Asymmetric synthesis
;
Hydrazones
;
Dehydroiridodiol
;
Dehydroiridodial
;
Cyclopentanoid monoterpenes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970308
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