Research Project
Grant-in-Aid for Young Scientists (B)
A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound.The new method has been applied to the stereoselective construction of the AB rings of the quinolizidine skeleton of sophoramine-type alkaloids with a cis-cis stereochemistry. The key features of this method involve: (i) the construction of the quinolizidine by the reduction of an acylpyridinium cation; and (ii) the late stage introduction of methoxypyridine by sequential Stille coupling and diastereoselective hydrogenation reactions.
All 2014 2013 2012 Other
All Journal Article (7 results) (of which Peer Reviewed: 6 results) Presentation (9 results) (of which Invited: 4 results) Remarks (6 results)
Synlett
Volume: 25 Issue: 05 Pages: 653-656
10.1055/s-0033-1340179
120005651944
Angew. Chem. Int. Ed.
Volume: 52 Pages: 1722-1722
Volume: 52 Issue: 39 Pages: 10204-10207
10.1002/anie.201305581
Volume: 52巻 Issue: 6 Pages: 1722-1725
10.1002/anie.201208297
Org. Lett.
Volume: 14 Issue: 16 Pages: 4270-4273
10.1021/ol302035j
Volume: 14 Issue: 7 Pages: 1902-1905
10.1021/ol300541u
Organic & Biomolecular Chemistry
Volume: 16(印刷中) Issue: 30 Pages: 6074-6086
10.1039/c2ob25111f
http://www.pharm.kyoto-u.ac.jp/orgchem/04_ron.html
http://www.pharm.kyoto-u.ac.jp/orgchem/05_gak.html