Methods for convenient asymmetric synthesis of c9-substituted steroid-like compounds
AssigneeTrustees of Dartmouth College
InventorGlenn C. MICALIZIO
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Abstract
The present disclosure relates to stereodefined polycyclic (e.g., tetracyclic) compounds that contain quaternary centers at one or multiple ring fusions, synthetic methods for preparing such compounds. In one aspect, the present disclosure relates to preparing a C9-alpha-substituted or a C9-beta-substituted compound (steroid numbering), the method comprising the steps of providing a tertiary allylic substrate and performing a regio- and stereoselective cyclization reaction to form a C9-C10 bond and to set a quaternary center at C9.
Claims20
A method for preparing a C9-alpha-substituted or a C9-beta-substituted steroid-like compound (steroid numbering), the method comprising the steps of providing a tertiary allylic substrate and performing a regio- and stereoselective cyclization reaction to form a C9—C10 bond and to set a quaternary center at C9, wherein the reaction is understood to likely proceed through a cationic intermediate to yield the C9-alpha-substituted steroid-like compound or the C9-beta-substituted steroid-like compound.
A method for preparing (a) a C9-alpha-substituted tetracyclic compound (steroid numbering), the method comprising a regio- and stereoselective cyclization reaction depicted in Scheme (1), Scheme (2), or Scheme (3):
- or
- (b) a C9-beta-substituted tetracyclic compound (steroid numbering), the method comprising a regio- and stereoselective cyclization reaction depicted in Scheme (4), Scheme (5), or Scheme (6):
A compound selected from the group consisting of a compound of Formula (Ei), Formula (Fi), Formula (Gi), Formula (Hi), Formula (Ji), Formula (Ki), Formula (Li), and Formula (Mi):
Dependencies are inferred from the claim text.