143954-86-3

Upstream product

• 50-00-0 formaldehyd 
• 189570-92-1 (+)-(2S,3S)-2-diethoxyphosphoryl-3-carboxycyclopentanone 
• 1469357-17-2 (3S)-(hex-1E-enyl)-2-hydroxymethylcyclopentanone 
• 1469357-19-4 (3S)-(hex-1E-enyl)-(2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone 
• 1469357-21-8 (2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone-(3R)-carboxylic acid 
• 930-30-3 cyclopent-2-enone 
• 143954-85-2 (+)-(3aR,6aS)-tetrahydro-1H-cyclopenta[c]furan-1,4(3H)-dione 
• 189570-93-2 (-)-(2R,3R)-2-diethoxyphosphoryl-3-carboxycyclopentanone 
• 155325-49-8 (S)-ethyl 3-oxocyclopentanecarboxylate 
• 143857-57-2 Hexaacetyl-3-formyloxy-4-hydroxycatalpol 
• 6910-20-9 Hexaacetylcatalpol 
• 143857-59-4 (1S,2R,3R,4R)-4-Acetoxy-3-(1,2-diacetoxyethyl)-1,2-bis(acetoxymethyl)-1-hydroxycyclopentan 
• 143857-60-7 (3aR,6R,6aR)-1,6-Dihydroxy-hexahydro-cyclopenta[c]furan-4-one 
• 143857-62-9 (3aR,6aS)-1-Methoxy-hexahydro-cyclopenta[c]furan-4-one 

Downstream Products

• 1909-79-1 2-methyl-2-cyclopenten-1-one-3-carboxylic acid 
• 777918-06-6 methyl (-)-trans-2-methylcyclopentan-3-one-1-carboxylate 

Relevant academic research and scientific papers

Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition

(R)-Sarkomycin was prepared using a five-step total synthesis. Key steps in the enantioselective construction of the targeted scaffold were a rhodium-catalyzed asymmetric conjugate alkenyl addition with subsequent silyl trapping and a Mukaiyama aldol reaction with aqueous formaldehyde. Protection of the hydroxy group as a THP acetal and oxidative cleavage of the C,C-double bond provided a stable direct precursor to the natural product. The final liberation was carried out under slightly acidic conditions in a microwave-assisted reaction, resulting in a high yield of the deceptive sarkomycin. This represents the shortest enantioselective synthesis of this rather unstable compound to date and the first to employ asymmetric catalysis to introduce the stereogenic center.

Total synthesis of racemic and optically active sarkomycin

trans-3-Carboxy-2-diethoxyphosphorylcyclopentanone (11), a key precursor of sarkomycin 1, has been synthesized in the rhodium(II) acetate promoted cyclization of diethyl 1-diazo-2-oxohept-6-enephosphonate (9), followed by transformation of the 3-vinyl moi

Chemistry and Stereochemistry of Iridoids, XVIII. - Enantiomerically Pure (+)-Cyclosarkomycin Catalpol

The reaction of hexaacetylcatalpol (2) with peroxyformic acid results in hexaacetyl-3-formyloxy-4-hydroxycatalpol (3), which is cleaved to 4 and sorbit (4a) by reduction with LiAlH4.The mixture of 4/4a was acetylated and the resulting acetates 5/5a separated by column chromatography.The following reactions from 5 to 9 (reactions e-i of Scheme 1) are each nearly quantitative.Therefore, the isolation of the intermediates 6-8 was not necessary.The constitutions of 6-8 were proven by 13C-NMR spectroscopy.The (1S,2RS,5R)-2-hydroxy-3-oxabicyclooctan-6-one (9) was purified by column chromatography and its oxidation by pyridinium chlorochromate (PCC) in dichloromethane leads to crystalline (+)-cyclosarkomycin (10) .Key Words: (+)-Cyclosarkomycin / Catalpol / Iridoids