Remote stereocontrol in [3, 3]-sigmatropic rearrangements: application to the total synthesis of the immunosuppressant mycestericin G
NWG Fairhurst, MF Mahon, RH Munday…
Index: Fairhurst, Nathan W. G.; Mahon, Mary F.; Munday, Rachel H.; Carbery, David R. Organic Letters, 2012 , vol. 14, # 3 p. 756 - 759
Full Text: HTML
Citation Number: 17
Abstract
The Ireland–Claisen [3, 3]-sigmatropic rearrangement has been used to access biologically important β, β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
Related Articles:
[Fujita, Tetsuro; Hamamichi, Norimitsu; Matsuzaki, Tohru; Kitao, Yuki; Kiuchi, Masatoshi; Node, Manabu; Hirose, Ryoji Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8599 - 8602]
[Fujita, Tetsuro; Hamamichi, Norimitsu; Matsuzaki, Tohru; Kitao, Yuki; Kiuchi, Masatoshi; Node, Manabu; Hirose, Ryoji Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8599 - 8602]
[Fujita, Tetsuro; Hamamichi, Norimitsu; Matsuzaki, Tohru; Kitao, Yuki; Kiuchi, Masatoshi; Node, Manabu; Hirose, Ryoji Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8599 - 8602]
[Fujita, Tetsuro; Hamamichi, Norimitsu; Matsuzaki, Tohru; Kitao, Yuki; Kiuchi, Masatoshi; Node, Manabu; Hirose, Ryoji Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8599 - 8602]
[Fujita, Tetsuro; Hamamichi, Norimitsu; Matsuzaki, Tohru; Kitao, Yuki; Kiuchi, Masatoshi; Node, Manabu; Hirose, Ryoji Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8599 - 8602]