Synthesis of ent-progesterone and intermediates thereof
AssigneesPrevacus, Inc., The Florida State University Research Foundation, Inc.
InventorsDaniel E. Levy, John W. Cran
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Abstract
The present invention relates to the synthesis of ent-progesterone and intermediates thereof.
Claims28
A method for preparing ent-progesterone, the method comprising the step of (a) reacting a compound of the formula U:
- to form a triketone intermediate of the formula U′:
- and
- (b) cyclizing the compound of formula U′ to form ent-progesterone.
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula A:
- with metal bromide to produce 5-bromopent-2-yne,
- wherein LG represents a leaving group.
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula D:
- with diisobutylaluminum hydride to form a compound of formula E:
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula V:
- with propargyl alcohol to form a compound of formula W
A method for preparing ent-progesterone, the method comprising the step of hydrogenating a compound of formula W:
- to form a compound of formula X
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula K:
- with a compound of formula M:
- to form a compound of formula N:
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula H:
- with a compound of formula S:
- to form a compound of formula T:
- wherein each instance of R is independently a C1-C4 straight or branched alkyl group, or a C3-C8 cycloalkyl group.
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula E:
- with a compound of formula R:
- to form a compound of formula T:
- wherein each instance of R is independently a C1-C4 straight or branched alkyl group, or a C3-C8 cycloalkyl group.
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula E:
- with a compound of formula Q:
- to form a compound of formula T:
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula I:
- with a compound of formula S:
- to form a compound of formula T:
A method for preparing ent-progesterone, the method comprising the step of reacting a compound of formula I:
- With a compound of formula Y:
- to form a compound of formula T:
A compound of the formula:
A method for preparing a compound of formula T:
- the method comprising reacting a compound of Formula I:
- with a compound of formula Y:
- in the presence of a base, thereby preparing the compound of formula T.
Dependencies are inferred from the claim text.