A microreview is presented of the development by the authors of the original preparation of enantiomerically pure cyclopentane blocks from the racemic [2+2]-cycloadducts of 1,3-cyclopentadiene and its derivatives with dichloroketene.
HudlickyT, PriceJD. (1989) Anionic approaches to the construction of cyclopentanoids. Chemical Reviews, 89, 1467–1486.
2.
TrostBM. (2004) Asymmetric allylic alkylation, an enabling methodology. The Journal of Organic Chemistry, 69, 5813–5837.
3.
MikołajczykM, MikinaM, ŹurawinskiR. (1999) Newphosphonate-mediated synthesis of cyclopentanoids and prostaglandins. Pure and Applied Chemistry, 71, 473–480.
4.
KrohnK. (1991) [4+1] and [3+2] Cycloadditions in the synthesis of cyclopentanoids. Organic Synthesis Highlights, 96–104.
5.
TrostBM. (1982) Cyclopentanoids: a challenge for new methodology. Chemical Society Reviews, 11, 141–170.
6.
CoreyEJ. (1988) Retrosynthetic thinking – essentials and examples. Chemical Society Reviews, 17, 111–133.
7.
GimazetdinovAM, GataullinSS, BushmarinovIS, MiftakhovMS. (2012) A simple and efficient synthesis of enantiomeric (3aRS,4RS,6aSR)-4-hydroxy-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]furan-1-ones. Tetrahedron, 68, 5754-5758 and references cited therein
CousinD, MannJ., (2008) A practical route to both enantiomers of bicyclo[3.3.0]oct-2-en-7-one and their use for the synthesis of key trisubstituted cyclopentanes. Tetrahedron, 64, 3534–3540.
10.
GovindanSV, HudlickyT, KoszykFJ. (1983) Two topologically distinct total syntheses of (±)-sarkomycin. The Journal of Organic Chemistry, 48, 3581–3583.
11.
Au-YeungB-W, WangY. (1985) Allylsilane in synthesis: new syntheses of (±)-desepoxy-4,5-didehydromethylenomycin a and (±)-xanthocidin. Journal of the Chemical Society. Chemical Communications, 12, 825–827.
12.
AlphandV, FurstossR., (1992) Microbial transformations 22. Microbiologically mediated Bayer-Villiger reactions: a unique route to several bicyclic γ–lactones in high enantiomeric purity. The Journal of Organic Chemistry, 57, 1306–1309.
13.
LebretonJ, AlphandV, FurstossR., (1997) Chemoenzymatic synthesis of marine brown pheromones. Tetrahedron, 53, 145–160.
14.
GimazetdinovAM, VostrikovNS, MiftakhovMS. (2008) Simple synthetic protocol for the preparation of enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones. Tetrahedron: Asymmetry, 19, 1094–1099.
15.
GimazetdinovAM, MiftakhovMS. (2009) Features of catalyzed hydration of 2-(dichloromethyl)-N-[(1R)-1-phenylethyl)]-cyclopent-3-ene-1-carboxamides. Russian Journal of Organic Chemistry, 45, 694–697.
ZanoniG, ReS, MerrigiA, CastranovoF, VidariG., (2001) Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations. Tetrahedron: Asymmetry, 12, 1785–1792.
18.
ZanoniG, PortaA, BrunoldiEM, VidariG., (2006) Asymmetric synthesis of a chiral building block for cyclopentanoids: a novel enantioselective synthesis of preclavulone A. The Journal of Organic Chemistry, 71, 8459–8466.
19.
ZanoniG, PortaA, CastranovoF, VidariG., (2003) First total synthesis of J2 isoprostane. The Journal of Organic Chemistry, 68, 6005–6010.
20.
ZanoniG, BrunoldiEM, PortaA, VidariG., (2007) Asymmetric synthesis of 14-A4t-neuroprostane: hunting for a suitable biomarker for neurodegenerative diseases. The Journal of Organic Chemistry, 72, 9698–9703.
21.
TietzeLF, StadlerC, BoehnkeN, BrasheG, GrubeA., (2007) Synthesis of enantiomerically pure cyclopentene building blocks. Synlett, 3, 485–487.
22.
TietzeLF, BrasheG, GrubeA, BoehnkeN, StadlerC., (2007) Synthesis of novel spinosyn A analogues by Pd-mediated transformations. Chemistry: A European Journal, 13, 8543–8563.
23.
TolstikovGA, MiftakhovMS, ValeevFA, VostricovNS, AkhmetvaleevRR. (1984) 7α-Formyloxy-8β-formyloxymethylen-cis-2-oxabicyclo[3.3.0]octan-3-on as a useful synthon in the synthesis of prostaglandins. Zhurnal Organicheskoi Khimii, 20, 1672–1675.
AndrauL, LebretonJ, ViazzoP, AlphandV, FurstossR., (1997) An integrated chemoenzymatic synthesis of enantiopure (-)-(1R,5S)-cyclosarkomycin: a sarcomycin precursor. Tetrahedron Letters, 38, 825–826.
26.
GimazetdinovAM, MiftakhovMS. (2010) Epoxy derivatives of {5-[(1-phenylethyl)aminocarbonyl]cyclopent-2-en-1-yl}methyl acetates. Russian Journal of Organic Chemistry, 46, 528–532.
27.
SungS-C. (1967) Sarcomycin. In Antibiotics. Springer, New York. 1, 156–170.
28.
KlausnerRD, DonaldsonJG, Lippincott-SchwartzJ. (1992) Brefeldin A: insights into the control of membrane traffic and organelle structure. Journal of Cell Biology, 116, 1071–1080.
29.
GimazetdinovAM, IshmurzinaGV, MiftakhovMS. (2012) Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A. Russian Journal of Organic Chemistry, 48, 8–17.
30.
MarxJN, MinaskanianG., (1982) Regiospecific synthesis of sarkomycin and some analogs. The Journal of Organic Chemistry, 47, 3306–3310.
RarigR-AF, ScheidemanM, VedejsE., (2008) Oxygen-directed intramolecular hydroboration. Journal of the American Chemical Society, 130, 9182–9183.
33.
FlemingI, Au-YeungB-W. (1981) The chemistry of an allylsilane – the synthesis of a prostaglandin intermediate and of loganin. Tetrahedron, 37, 13–24.
34.
IvanovaNA, AkhmetdinovaNP, ValiullinaZR, Akhmt'yanovaVA, ShitikovaOV, LobovAN, SuponitskiiKYu, SpirikhinLV, MiftakhovMS. (2012) Chiral blocks for the synthesis of cyclopentanoids from [2+2]-cycloadduct of dichloroketene and dimethylfulvene. Russian Journal of Organic Chemistry, 48, 442–450.
35.
AkhmetdinovaNP, ValiullinaZR, IvanovaNA, ShitikovaOV, MiftakhovMS. (2011) Syntheses and oxidative transformations of 6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one and its precursors. Russian Journal of Organic Chemistry, 47, 185–191.
36.
JohansenSK, LundtI., (1999) Synthesis of carbosugars from aldolactones. Part II. Preparation of polyhydroxyaminocyclopentanes functionalized at all five ring carbons. Journal of the Chemical Society. Perkin Transactions I, 3615–3622.
37.
DasS, ChandrasekharS, SinghYJ, GréeR. (2007) Recent developments in the synthesis of prostaglandins and analogues. Chemical Reviews, 107, 3286–3337.
38.
CrimminsMT. (1998) New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron, 54, 9229–9272.
39.
MartínesAG, VilarET, FraileAG, CereroSM, OsunaSO, MarotoBL. (2002) From natural camphor to (1R,2S)-2-chloromethyl-3-oxocyclopentanecarboxylic acid: a stereocontrolled approach to enantiopure sarkomycin. Tetrahedron Letters, 42, 7795–7799.
