145107-27-3Relevant articles and documents
A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol
Ananthan, Bakthavachalam,Chang, Wan-Chun,Lin, Jhe-Sain,Li, Pin-Hui,Yan, Tu-Hsin
, p. 2898 - 2905 (2014/05/06)
Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (±)-Clivonine via a biomimetic ring-switch from a lycorine-type progenitor
Giro Mannas, Carles,Paddock, Victoria L.,Bochet, Christian G.,Spivey, Alan C.,White, Andrew J. P.,Mann, Inderjit,Oppolzer, Wolfgang
supporting information; experimental part, p. 5176 - 5178 (2010/06/18)
A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
Chemoenzymatic synthesis of glycosyl-deoxyinositol derivatives. First example of a fagopyritol β-analogue containing an aminoinositol unit
Bellomo, Ana,Bonilla, Julia B.,Lopez-Prados, Javier,Martin-Lomas, Manuel,Gonzalez, David
scheme or table, p. 2061 - 2064 (2010/03/01)
The first synthesis of two fagopyritol β-analogues (β-d-galactopyranosyl-(1′→1)-conduramine F-4 and β-d-galactopyranosyl-(1′→3)-4-aminodeoxy-l-chiro-inosito l) has been accomplished by a chemoenzymatic route in satisfactory yields. The key step of the synthesis is the TMSOTf-promoted glycosylation reaction of a deoxyconduritol derivative. The methodology is amenable to scale-up and expandable to the preparation of other pseudofagopyritols.
Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols
Bellomo, Ana,Camarano, Soledad,Rossini, Carmen,Gonzalez, David
scheme or table, p. 44 - 51 (2011/03/20)
The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-l-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequen
Novel deoxy-selenylconduritols: chemoenzymatic synthesis and biological evaluation
Bellomo, Ana,Bertucci, Ana,Stefani, Helio,Vazquez, Alvaro,Gonzalez, David
scheme or table, p. 2673 - 2676 (2010/04/29)
The first synthesis of two selenyldeoxycyclitols (4-bromo-2-phenylselenyl conduritol F and 6-phenylselenylconduritol F) is reported via a chemoenzymatic enantioselective route. The key step of the synthesis is the selenolysis of a vinyl epoxide. The new compounds were evaluated for their capacity to inhibit the growth of different microorganisms using a modification of the agar diffusion technique with thin layer chromatography plates as support.
Use of Electrochemical Methods as an Alternative to Tin Reagents for the Reduction of Vinyl Halides in Inositol Synthons
Hudlicky, Tomas,Claeboe, Christopher D.,Brammer Jr., Larry E.,Koroniak, Lukasz,Butora, Gabor,Ghiviriga, Ion
, p. 4909 - 4913 (2007/10/03)
Several vinyl halides previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the selective reduction of vinyl halides to olefins. Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology. Cinnamyl ethers were reductively cleaved at -3.2 V (vs Ag/AgNO3) in the presence of alkyl allyl ethers to provide selective deprotection. The electrochemical reduction of vinyl halides in the presence of a vinyloxirane or vinylaziridine is accompanied by the solvolysis of the strained rings. Yields and conditions are reported and compared to those from standard tin-induced dehalogenation.
Regio- and stereo-chemical outcomes in the nucleophilic ring cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols
Banwell, Martin G.,Haddad, Najiba,Hudlicky, Tomas,Nugent, Thomas C.,Mackay, Maureen F.,Richards, Sharon L.
, p. 1779 - 1791 (2007/10/03)
Reactions of the mono-epoxy derivatives, 4-7, of the cis-1,2-dihydrocatechols 1 and 2 with various oxygen-, nitrogen-, carbon- and halogen-centred nucleophiles have been studied. In both direct and acid-catalysed processes these epoxides react exclusively
Stereospecific synthesis of conduramine-F4 and conduritol-F (Leucanthemitol)
Secen,Gultekin,Sutbeyaz,Balci
, p. 2103 - 2108 (2007/10/02)
Stereospecific synthesis of Conduramine-F4 and Conduritol-F has been achieved by fully stereospecific cyloaddition of singlet oxygen to cyclohexadiene ketal 1 followed by reductive extrusion of one oxygen atom. The obtained monoepoxide 3 has be
COMPLEMENTARY ENANTIOSPECIFIC SYNTHESES OF CONDURITOL E EPOXIDES FROM HALOBENZENES
Carless, Howard A. J.
, p. 6379 - 6382 (2007/10/02)
Microbial oxidation of chlorobenzene and bromobenzene gave diols (3), which were converted in stereoselective and chemoselective sequences involving epoxidation/osmylation steps and reduction to the enantiomers of (-)- or (+)-conduritol E epoxide (4).
