Synthetic studies toward highly functionalized 5beta-lanosterol derivatives: a versatile approach utilizing anionic cycloaddition.
Stereoselective synthesis of the potentially biologically valuable 5beta-lanosteroidal-type backbone was achieved via anionic cycloaddition. Synthesis of the two new bicyclic Nazarov intermediates 14 and 40 and their cycloaddition with chiral cyclohexenone 25 and further functional group manipulations resulted in highly functionalized tetracyclic intermediates 28 and 44. These synthetic intermediates could lead to the total synthesis of new lanosterol-based inhibitors.
Ramachandran
Sreekanth A
SA
Laboratoire de Synthèse Organique, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada, and Département de Chimie, Faculté des Sciences et de Génie Université Laval, Québec G1K 7P4, Canada.
Kharul
Rajendra K
RK
Lepage
Olivier
O
Marque
Sylvain
S
Soucy
Pierre
P
Jacques
Frédéric
F
Chênevert
Robert
R
Deslongchamps
Pierre
P
D000586:Amination; D000838:Anions / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry; D001389:Azirines / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D010758:Phosphorus / Q000737:chemistry
D000838:Anions; D001388:Aziridines; D001389:Azirines; D010091:Oximes; D007810:Lanosterol; D010758:Phosphorus; D005461:Fluorine; C033132:aziridine