US4059593A
Expired / Lapsed
US
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Synthesis of steganacin and derivatives thereof
Assignee: University of Rochester
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Filing: 1976-08-18
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Granted: 1977-11-22
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Expires: 1996-08-18
Abstract
Abstract Steganacin and Steganangin, dibenzocyclooctadiene lignan lactones, have been reported to possess anti-leukemic activity. This invention describes the first total synthesis of these compounds and other relevant intermediates.
Inventors
- 👤 Andrew S. Kende
- 👤 Lanny S. Liebeskind
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 01:31
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/60; C07D317/54; C07D317/70
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
237 words
A process for the preparation of a racemic mixture of the compound having the formula ##STR63## in which Z is OH, oxo (═O) or OW wherein W is acetyl or ##STR64## and R 1 , R 2 and R 3 are alike or different and each is H or (lower)alkyl of 1 to 3 carbon atoms, which process comprises the consecutive steps of A. treating the compound having the formula ##STR65## in which R 1 , R 2 and R 3 are as defined above, with excess 37% aqueous formaldehdye in the presence of 0.1-2.0M alkali metal hydroxide for about 1 to 48 hours, followed by heating in the presence of excess dilute sulfuric acid and chloroform to produce the compound having the formula ##STR66## in which R 1 , R 2 and R 3 are as defined above; B. treating compound IV with sodium borohydride in methylene chloride-anhydrous methanol to produce a mixture of the compounds having the formula ##STR67## in which R 1 , R 2 and R 3 are as defined above, which mixture is separated into its component parts; C. acylating compound III with acetic anhydride, acetyl halide or angelic acid halide in the presence of a tertiary amine to produce the compound having the formula ##STR68## in which W is acetyl or ##STR69## R 1 , R 2 and R 3 are as defined above and halide is Cl, Br or I.
Claim 2
Dependent Claim
237 words
A process for the preparation of a racemic mixture of the compound having the formula ##STR63## in which Z is OH, oxo (═O) or OW wherein W is acetyl or ##STR64## and R 1 , R 2 and R 3 are alike or different and each is H or (lower)alkyl of 1 to 3 carbon atoms, which process comprises the consecutive steps of A. treating the compound having the formula ##STR65## in which R 1 , R 2 and R 3 are as defined above, with excess 37% aqueous formaldehdye in the presence of 0.1-2.0M alkali metal hydroxide for about 1 to 48 hours, followed by heating in the presence of excess dilute sulfuric acid and chloroform to produce the compound having the formula ##STR66## in which R 1 , R 2 and R 3 are as defined above; B. treating compound IV with sodium borohydride in methylene chloride-anhydrous methanol to produce a mixture of the compounds having the formula ##STR67## in which R 1 , R 2 and R 3 are as defined above, which mixture is separated into its component parts; C. acylating compound III with acetic anhydride, acetyl halide or angelic acid halide in the presence of a tertiary amine to produce the compound having the formula ##STR68## in which W is acetyl or ##STR69## R 1 , R 2 and R 3 are as defined above and halide is Cl, Br or I.
Claim 3
Dependent Claim
167 words
The process of claim 1 for the preparation of a racemic mixture of the compound having the formula ##STR70## which process comprises the consecutive steps of A. treating the compound having the formula ##STR71## with a 25% molar excess of 37% aqueous formaldehyde in the presence of excess 1N sodium hydroxide at about room temperature for about 1 to 48 hours, followed by heating in the presence of excess 10% sulfuric acid and chloroform to produce the compound having the formula ##STR72## B. treating compound IV with a slight molar excess of sodium borohydride in methylene chloride-anhydrous methanol for about 1 to 5 minutes, followed by quenching in water, to produce a mixture of the compounds having the formula ##STR73## which mixture is separated into its component parts; and C. acylating compound III with acetic anhydride or acetyl chloride in the presence of a tertiary amine selected from the group consisting of pryidine, trimethylamine, triethylamine, dimethylaniline and n-methylpiperidine with the aid of heat to produce compound I.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |