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Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69
Graphical Abstract
Scheme 1: The diastereoselective intramolecular Heck-hydrogenation and double reduction sequence as a means o...
Scheme 2: The synthesis of 5a and 5b by an intramolecular Heck cyclisation reaction.
Scheme 3: Diastereoselective epoxidation of 5a and 5b.
Figure 1: X-ray structure of 7a; including a view along the S=O···C–O axis (Diamond representations) [O2···C9...
Scheme 4: cis-Selective dibromination of 5a (NOE indicated by arrows).
Figure 2: X-ray crystal structure of 13a (Diamond representation).
Scheme 5: Dibromination studies of 5b.
Figure 3: X-ray crystal structures of 18b and 19b (Diamond representations).
Scheme 6: Possible explanation for the products formed in the dibromination of 5a and 5b.
Scheme 7: Lithiation–CO2 quench approach for the synthesis of 26 from vinyl bromide 24a.
Figure 4: X-ray structure of 26 (Diamond representation).
Scheme 8: Suzuki–Miyaura cross-coupling of 24a and the diastereoselective hydrogenation of the resultant styr...
Figure 5: X-ray crystal structure of 31 (Diamond representation).
Scheme 9: Attempted sulfonamide double reduction of compounds 31–34.