39643-60-2

Upstream product

• 4729-05-9 endo-bicyclo[3.1.0]hex-2-ene-6-carbaldehyde 
• 278-06-8 tetracyclo-[3.2.0.0.^2,7.0^4,6]heptane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 5307-99-3 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 20836-85-5 7-endo-chlorobicyclo<3.2.0>hept-2-en-6-one 
• 53670-43-2 (1R,5S,6S,7R)-7-Chloro-bicyclo[3.2.0]hept-2-en-6-ol 

Downstream Products

• 4971-26-0 1α,5α,6α-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid 

Relevant academic research and scientific papers

Generation of [5.5.n] Tricyclic Ring Systems by Radical-Promoted Inter- And Intramolecular [3 + 2] Cycloadditions

A new method for the synthesis of [5.5.n] tricyclic ring systems via radical fragmentation and double cyclization is described. The general process (Scheme 1) involves addition of an alkylthio radical to an alkenylcyclopropane 1 to generate the cyclopropylcarbinyl radical which opens to the homoallylic radical; this radical then adds to an alkene or alkyne radical trap to give a new alkyl radical which then adds back to the thioalkyl allylic system to generate, after loss of the alkylthio radical, the bi- or tricyclic product, 2, thus making the process analogous to a [3 + 2] cycloaddition. Thus addition of the butylthio radical (generated by photolysis of dibutyl disulfide) to the bicyclo-[3.1.0]hex-2-en-6-yl carboxylate 3 in the presence of an alkene or alkyne-either an acyclic radical trap, e.g., ethyl vinyl ether, isopropenyl acetate, methyl acrytate, or methyl propiolate, or a cyclic one, e.g., cyclopentenone, dihydrofuran, cyclopentenyl acetate, or cyclopentene-affords the desired bi- or tricyclic products 9-16 in yields of 54-88%. One can also use 6-vinylbicyclo[3.1.0]hexan-2-one (4) as the alkenylcyclopropane unit. Trapping of the radical generated by addition of butylthio radical to 4 with ethyl vinyl ether or cyclopentene affords the bi- and tricyclic products 17 and 18 in 66-68% yields. The products are formed as diastereomeric mixtures in all cases. This cyclization process can also be carried out in an intramolecular fashion, e.g., isomerization of the ketones 25 and 27 or the esters 28-30 with butylthio radical to give the tricyclic products 31-35 and 41-43. The use of dimethyl-substituted alkenes gives reasonably good diastereoselectivity favoring the cis-syn-cis isomer over the cis-anti-cis isomer, e.g., 7.5:1 for 33 over 34 and 4.2:1 for 41 over 42. The structures of the diastereomeric products were proven by comparison of the NMR spectra of the saturated analogues, which are known for the unsubstituted series and differ in their symmetry properties for the dimethyl-substituted case. These results indicate that the cyclization of a stabilized 5-hexenyl radical, e.g., 45 in Scheme 8, is reversible and leads to the most stable final product.

PYRAZOLYLPYRIDINE ANTIVIRAL AGENTS

Provided are compounds of Formula (I) and/or Formula (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

An efficient synthesis of (±)-cis-2-mino-6-hydroxy-9[4'-hydroxyethyl- 2'-cyclopenten-1'-yl]purine

The synthesis of a carbovir analogue, (±)-cis-2-amino-6-hydroxy-9- [4'hydroxyethyl-2'-cyclopenten-l'-yl]purine (2) was achieved from 2,5- norbornadiene (3) in six steps and 31% overall yield. This route involves a Meinwald rearrangement, one-pot operation (acid-hydrolysis and subsequent sodium borohydride reduction), and a Pd(0)catalyzed coupling reaction.

2-Decarboxy-2-amino-methyl-PGE and PGD analogs

Prostaglandin analogs wherein the C-2 carboxy is replaced by an aminomethyl or (substituted amino)methyl are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for the same pharmacological purposes as the prostaglandins.

Aliphatic 2-decarboxy-2-hydroxymethyl-13,14-didehydro-PG compounds

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

13,14-Didehydro-PG3 compounds

This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

PGF1β -oxa phenylene compounds

This invention is a group of PGF1β -type and PGF2β -type oxa-phenylene compounds, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including inhibition of platelet aggregation, treatment of asthma, labor inducement at term, and cervical dilation.