Total synthesis of (±)-jiadifenin, a non-peptidyl neurotrophic modulator

Journal of the American Chemical Society

Volumn 126, Issue 44, 2004, Pages 14358-14359

  Cho, Young Shin ^a   Carcache, David A ^a   Tian, Yuan ^a   Li, Yue Ming ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEXANEDIONE ETHYLENE KETAL; ACETAL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; HYDROXY 3,4 DEHYDRONEOMANJUCIN; JIADIFENIN; KETONE DERIVATIVE; NEUROTROPHIC FACTOR; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; NERVE GROWTH FACTOR; SESQUITERPENE;

ANIMAL CELL; ARTICLE; BRAIN CELL; BROMINATION; CONTROLLED STUDY; CYCLIZATION; DEPROTECTION REACTION; DIASTEREOISOMER; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; ILLICIUM; ILLICIUM JIADIFENGPI; METHYLATION; NERVE FIBER GROWTH; NONHUMAN; OXIDATION; RAT; REDUCTION; REPRODUCIBILITY; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; ANIMAL; CELL STRAIN; DRUG EFFECT; NEURITE; SYNTHESIS;

ANIMALS; NERVE GROWTH FACTORS; NEURITES; PC12 CELLS; RATS; SESQUITERPENES;

EID: 7744244618     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045939p     Document Type: Article

References (17)

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14. (a) Incorporation of the C(10) hydroxyl group was hampered by decomposition of both starting compound and product under the reaction conditions. Accordingly, it was necessary to cease the reaction well before the conclusion. We isolated the desired product 16 and the starting material in 26% and 73% yield, respectively. The recovered starting material was resubmitted to the reaction conditions to give 16 in 42% combined yield after one recycle.
15. (b) A mixture of diastereomers was observed at C(10) of 16 (6:1 ratio, a major diastereomer as shown in 16).
16. Rat pheochromocytoma cells (PC 12) were cultured in a 96-well collagen-coated plate in F-12K medium supplemented with 0.5% fetal calf serum and 50 ng/mL of NGF (2.5 S) with or without each compound at 0.3 μM in DMSO solution for 48 h. Fresh medium with the same supplements was placed on the cell for an additional 48 h. The cells were then fixed and examined by microscopy. From our PC-12 assay, the neunte outgrowth associated with neuronal differentiation was determined.
17. In the absence of NGF, no neurite outgrowth was observed.