117957-61-6

Basic information

• Product Name: (3aSR,5R,6aR)-(+)-5-Hydroxy-hexahydro-2H-cyclopentafuran-2-on

Upstream product

• 13173-09-6 bicyclo[3.2.0]hept-2-en-6-one 
• 56011-39-3 (1R*,2S*,3S*,5R*)-(±)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 694-98-4 norborn-5-en-2-one 
• 56460-52-7 1β,5β,7α,8β-7-hydroxy-8-iodo-2-oxabicyclo<3.3.0>octan-3-one 
• 74877-19-3 cis-2-(4-hydroxycyclopent-2-enyl)acetic acid 

Downstream Products

• 1357495-82-9 benzyl 2-(6-oxo-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-4-yl)-acetate 
• 158604-58-1 benzyl 2-(4-oxocyclopent-2-en-1-yl)acetate 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Relevant articles and documents

Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition

The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.

SYNTHESIS OF NOVEL BICYCLIC ALCOHOLS AND THEIR NITRATES

1(R),5(S)-2-oxa-bicyclooct-6-en-3-one (2), a chiral by-product of the manufacture of prostaglandin derivatives, is easily converted into the alcohols (5a), (6a), (6c) and nitrates (5b), (6b), and (6d).Regio- and stereoisomers were identified on the basis of their NMR spectra.

Synthesis of 2,4-Diazabicyclooctane-3,7-diones and 3-Thioxo-2,4-diazabicyclooctan-7-one by an Intramolecular Michael-type Reaction. Stability of 2,4 Diaza-, 4-Oxa-2-aza-, and 4-Thia-2-aza-bicyclooctane-3,7-diones

Novel 2,4-diazabicyclooctane-3,7-diones (10) have been prepared by an intramolecular Micael-type cyclisation.The analogous 3-thioxo-2,4-diazabicyclooctan-7-one system (20) is obtained by base-catalysed retro-Michael reaction of the less stable 3-arylimino-2-thia-4-azabicyclooctan-7-one isomer (19).The 2-aza-4-oxabicyclooctane-3,7-dione system (17) is shown to be very unstable to base, fragmenting via the carbamic acid to give carbon dioxide and a 4-N-substituted cyclopent-2-enone (11).The relative stability to base of these bicyclic systems is correlated with their structure.