DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (-)-OUDEMANSIN-AVIA [2,3]-WITTIG REARRANGEMENT OF CROTYLOXYACETALDEHYDE-SAEP-HYDRAZONE

Authors
ENDERS D BARTSCH M BACKHAUS D
Citation
D. Enders et al., DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (-)-OUDEMANSIN-AVIA [2,3]-WITTIG REARRANGEMENT OF CROTYLOXYACETALDEHYDE-SAEP-HYDRAZONE, Synlett, (8), 1995, pp. 869-870
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1995
Pages
869 - 870
Database
ISI
SICI code
0936-5214(1995):8<869:DAESO(>2.0.ZU;2-W
Abstract
The total synthesis of (-)-oudemansin A (1) was accomplished in a ten - step sequence with good overall yield (20%) and excellent diastereo- and enantiomeric excesses (de, ee greater than or equal to 98%). Key step of the synthesis is the asymmetric [2,3]-Wittig rearrangement of crotyloxyacetaldehyde-SAEP-hydrazone [(S)-6].