11031-48-4Relevant articles and documents
Simple Routes to Sarkomycin
Kodpinid, Montree,Siwapinyoyos, Tiwa,Thebtaranonth, Yodhathai
, p. 4862 - 4865 (1984)
Two synthetic routes to sarkomycin (6) are demonstrated.The first involves a 3-carbon annelation to form the spirocyclopentenone (2) followed by regiospecific γ-alkylation and subsequent manipulation of the side chain in 15 to give the sarkomycin ester adduct 18.The second route employs the itaconate-anthracene adduct 20 as the C-5 synthon in a tandem Michael addition-Dieckmann condensation between the anion derived from 20 and methyl acrylate.The reaction furnishes the diester 22, which, upon selective decarboxylation, gives rise to the sarkomycin precursors 18 and 23 (1:3).Flash vacuum pyrolysis of either isomer 18 or 23 yields (+/-)-sarkomycin ester 7 which is then hydrolyzed to the acid 6.
A simple synthesis of (±)-sarkomycin
Kar, Anirban,Argade, Narshinha P.
, p. 1234 - 1236 (2005)
A facile 6-step route to (±)-sarkomycin in 17% overall yield has been described via Michael addition of nitromethane to 2-hydroxymethyl-2- cyclopentenone, oxone-induced oxidative Nef reaction, and acid catalyzed dehydration. Georg Thieme Verlag Stuttgart.
A NEW SYNTHESIS OF (+/-)-SARKOMYCIN FROM A β-KETOPHOSPHONATE
Mikolajczyk, Marian,Zurawinski, Remigiusz,Kielbasinski, Piotr
, p. 1143 - 1146 (1989)
The total synthesis of (+/-)-sarkomycin starting from diehtyl 2-oxopropanephosphonate is reported.The key step in this synthesis includes the Horner-Wittig reaction of 2-diethoxy-phosphoryl-3-carboxy-cyclopentanone with formaldehyde
Efficient Enantioselective Synthesis of the Antitumor Agent Sarkomycin
Boeckman, Robert K.,Naegely, Paul C.,Arthur, Samuel D.
, p. 752 - 754 (1980)
An efficient total synthesis of (+/-)-sarkomycin (1) is described via bicyclic lactone 8.Preparation of a key precursor (R)-(+)-6 via an asymmetric Diels-Alder reaction affords the correct enantiomer for the preparation of natural (R)-(-)-sarkomycin (1) in high optical yield.
Total synthesis of racemic and optically active sarkomycin
Miko?ajczyk, Marian,Zurawiński, Remigiusz,Kie?basin?ski, Piotr,Wieczorek, Micha? W.,B?aszczyk, Jaros?aw,Majzner, Wies?aw R.
, p. 356 - 365 (1997)
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
CONJUGATE ADDITION TO THE ETHYLENE KETAL OF 2-CARBOMETHOXY-2-CYCLOPENTENONE A SYNTHESIS OF SARKOMYCIN
Hewson, Alan T.,MacPherson, David T.
, p. 647 - 648 (1983)
1,4-addition of nitronate anions to the title ketal ester (III) is described; one of the adducts is converted to sarkomycin.
Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition
Westmeier, Johannes,Kress, Steffen,Pfaff, Christopher,Von Zezschwitz, Paultheo
, p. 10718 - 10723 (2013/11/19)
(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.
Compound having effect of promoting neuron differentiation
-
, (2008/06/13)
A novel cystacycline derivative which has an excellent effect of promoting the differentiation of neurons and is useful as a remedy for central nervous system disorders, a remedy for peripheral nerve disorders, etc.
Chemistry and Stereochemistry of Iridoids, XVIII. - Enantiomerically Pure (+)-Cyclosarkomycin Catalpol
Weinges, Klaus,Ziegler, Hans Juergen,Schick, Hartmut
, p. 1213 - 1216 (2007/10/02)
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
α-PHOSPHORYL CYCLOPENTANONES AS POSSIBLE INTERMEDIATES IN THE TOTAL SYNTHESIS OF SARKOMYCIN
Mikolajczyk, Marian,Kielbasinski, Piotr,Zurawinski, Remigtusz,Wieczorek, Michal W.
, p. 97 - 100 (2007/10/02)
In an effort to synthesize sarkomycin 1 trans-2-diphenylphosphinoyl-3-tris(methylthio)methyl-cyclopentanone 7 and trans-2-diphenylphosphinoyl-3-carbomethoxy-cyclopentanone 8 were prepared.The Horner-Wittig reaction of the latter with formaldehyde failed.
