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US4219489A
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Synthesis of steroids
Assignee: Leland Stanford Junior University
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Filing: 1978-09-05
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Granted: 1980-08-26
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Expires: 1998-09-05
Abstract
Abstract Method and compounds are provided for use in the synthesis of steroids wherein a polyolefin is provided having an initiating group having a chalcogen atom in juxtaposition to a double bond, so as to be capable of bond formation to close to form a ring and having a terminating group involving pi unsaturation (a double or triple bond) conjugated to an aromatic ring. Upon acid catalysis, sigma bonds are formed through the interaction of a carbocation formed at the carbon atom bonded to the chalcogen atom and the double bond intermediate the initiating group and the terminating group, which close to form rings of a steroid nucleus, the carbocation interacting with the pi unsaturation conjugated with the aromatic group and being captured by a nucleophile present in the acidic reaction medium. The resulting steroid product may then be modified in known ways to produce known steroids.
Inventors
- 👤 William S. Johnson
- 👤 Leonard A. Bunes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:27
CPC Classifications
C; C07; C07J; C07J61/00; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/103; C07C29/132; C07C29/136; C07C29/147; C07C29/36; C07C29/38; C07C29/40; C07C29/58; C07C33/00; C07C33/28; C07C33/30; C07C35/00; C07C35/21; C07C403/00; C07C403/02; C07C45/00; C07C45/27; C07C45/29; C07C45/292; C07C45/56; C07C45/57; C07C45/59; C07C45/61; C07C45/65; C07C45/66; C07C45/67; C07C45/673; C07C45/676; C07D; C07D309/00; C07D309/02; C07D309/08; C07D317/00; C07D317/08; C07D317/10; C07D317/12; C07D339/00; C07D339/02; C07D339/06; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/655; C07F9/65525; C07J1/00; C07J1/0003; C07J1/0011; C07J1/0014; C07J11/00; C07J9/00; C07B; C07B2200/00; C07B2200/09; C07C2601/00; C07C2601/02; C07C2601/12; C07C2601/16; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/24
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
43 words
A compound of the formula ##STR16## wherein: Ar is phenyl, naphthyl or substituted phenyl, wherein said substituent is alkyl of from 1 to 4 carbon atoms, hydroxy, thiol, alkoxy of up to 4 carbon atoms, or alkylthio of up to 4 carbon atoms.
Claim 2
Dependent Claim
43 words
A compound of the formula ##STR16## wherein: Ar is phenyl, naphthyl or substituted phenyl, wherein said substituent is alkyl of from 1 to 4 carbon atoms, hydroxy, thiol, alkoxy of up to 4 carbon atoms, or alkylthio of up to 4 carbon atoms.
Claim 3
Dependent Claim
57 words
A compound of the formula ##STR17## wherein: Ar is phenyl, substituted phenyl, wherein the substituent is alkyl of from 1 to 4 carbon atoms, hydroxy, thiol, alkoxy or alkylthio of up to 4 carbon atoms, or naphthyl; and t and t' may be taken together to form a bond or t is methyl and t' is hydrogen.
Claim 4
Dependent Claim
57 words
A compound of the formula ##STR17## wherein: Ar is phenyl, substituted phenyl, wherein the substituent is alkyl of from 1 to 4 carbon atoms, hydroxy, thiol, alkoxy or alkylthio of up to 4 carbon atoms, or naphthyl; and t and t' may be taken together to form a bond or t is methyl and t' is hydrogen.
Claim 5
Dependent Claim
136 words
A compound which is a member of the group consisting of: (1) a compound of the formula: ##STR18## or (2) a compound of the formula: ##STR19## wherein: a is hydrogen or methyl; b is hydrogen or methyl; e is hydrogen, methyl, hydroxy or alkoxy of up to 6 carbon atoms; Ar is a carbocyclic aromatic compound of from 6 to 12 annular carbon atoms having from 0 to 2 substituents, said substituents selected from the group consisting of hydroxy, thiol, alkoxy of up to 4 carbon atoms, alkylthio of up to 4 carbon atoms, and alkyl of from 1 to 4 carbon atoms; 1is hydroxy and k' is hydrogen, with the proviso that 1 and k' may be taken together to define oxo; and t is hydrogen or alkyl of from 1 to 2 carbon atoms.
Claim 6
Dependent Claim
136 words
A compound which is a member of the group consisting of: (1) a compound of the formula: ##STR18## or (2) a compound of the formula: ##STR19## wherein: a is hydrogen or methyl; b is hydrogen or methyl; e is hydrogen, methyl, hydroxy or alkoxy of up to 6 carbon atoms; Ar is a carbocyclic aromatic compound of from 6 to 12 annular carbon atoms having from 0 to 2 substituents, said substituents selected from the group consisting of hydroxy, thiol, alkoxy of up to 4 carbon atoms, alkylthio of up to 4 carbon atoms, and alkyl of from 1 to 4 carbon atoms; 1is hydroxy and k' is hydrogen, with the proviso that 1 and k' may be taken together to define oxo; and t is hydrogen or alkyl of from 1 to 2 carbon atoms.
Claim 7
Dependent Claim
19 words
A compound according to claim 3, which is of formula (1), where t is methyl and e is hydrogen.
Claim 8
Dependent Claim
12 words
A compound according to claim 4, wherein a and b are methyl.
Claim 9
Dependent Claim
15 words
A compound according to claim 3, which is of formula (2) and e is hydrogen.
Claim 10
Dependent Claim
12 words
A compound according to claim 6, wherein a and b are methyl.
Claim 11
Dependent Claim
132 words
A precursor to a compound according to claim 3, which is a member of the group consisting of: (1) a compound of the formula: ##STR20## or (2) a compound of the formula: ##STR21## wherein: a and b are hydrogen or methyl; e is hydrogen, methyl, hydroxy, or alkoxy of up to 6 carbon atoms; Ar is a carbocyclic aromatic compound of from 6 to 12 annular carbon atoms having from 0 to 2 substituents, said substituents selected from the group consisting of hydroxy, thiol, alkoxy of up to 4 carbon atoms, alkylthio of up to 4 carbon atoms, and alkyl of from 1 to 4 carbon atoms; j and k are hydrogen or are taken together to form a bond; and t and t' are the same as defined in claim 2.
References Cited (Backward Citations)
US3884945A
Cited
US4032579A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-08-26 | 1984-02-25 | 1984-08-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-08-26 | 1988-02-25 | 1988-08-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-08-26 | 1992-02-25 | 1992-08-26 | $7700.00 | Window Closed / Lapsed |