321164-63-0Relevant academic research and scientific papers
Syntheses of Dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 via Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols
Brennan, Méabh B.,Csatayová, Kristína,Davies, Stephen G.,Fletcher, Ai M.,Green, William D.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
, p. 6609 - 6618 (2015)
Diastereoselective syntheses of dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 have been achieved from N-protected 4-aminocyclohex-2-en-1-ols via two complementary procedures for epoxidation as the key step. Treatment of either trans- or cis-4-N-benzylaminocyclohex-2-en-1-ol with Cl3CCO2H and then m-chloroperoxybenzoic acid (m-CPBA) resulted in initial formation of the corresponding ammonium species, followed by epoxidation on the face syn to the ammonium moiety exclusively; chemoselective N-benzylation then provided either (1RS,2SR,3RS,4RS)- or (1RS,2RS,3SR,4SR)-2,3-epoxy-4-N,N-dibenzylaminocyclohexan-1-ol, respectively. Treatment of either trans- or cis-4-N,N-dibenzylaminocyclohex-2-en-1-ol with m-CPBA resulted in initial formation of the corresponding N-oxide, followed by epoxidation on the face syn to the hydroxyl group exclusively; reduction then provided either (1RS,2RS,3SR,4RS)- or an alternative route to (1RS,2RS,3SR,4SR)-2,3-epoxy-4-N,N-dibenzylaminocyclohexan-1-ol, respectively. In all cases, SN2-type ring opening of these epoxides upon treatment with aqueous H2SO4 proceeded by nucleophilic attack with inversion at C(2) preferentially, distal to the in situ formed ammonium moiety. Hydrogenolytic N-deprotection then gave the corresponding dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1.
Synthesis of (-)-Conduramine A1, (-)-Conduramine A2 and (-)-Conduramine E2 in Six Steps from Cyclohexa-1,4-diene
Da Silva Pinto, Solange,Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.
, p. 7933 - 7937 (2019/10/10)
A method to enable the synthesis of conduramines and their N-substituted derivatives (enantiopure or racemic form) in six steps (five steps for N-substituted derivatives) from cyclohexa-1,4-diene is reported. Key features of this reaction sequence include a preparation of benzene oxide that is amenable to multigram scale, and its efficient ring-opening upon treatment with a primary amine. Epoxidation of the resultant amino alcohols (40% aq HBF4 then m-CPBA) is accompanied by hydrolytic ring-opening in situ to give the corresponding N-substituted conduramine derivatives directly. These may undergo subsequent N-deprotection to give the parent conduramines, as demonstrated by the preparation of enantiopure (-)-conduramine A1, (-)-conduramine A2, and (-)-conduramine E2 (the latter two for the first time). The selectivity of the epoxidation reaction is proposed to be the result of competitive ammonium-directed and hydroxyl-directed epoxidation processes, followed by either direct (SN2-type) or conjugate (SN2′-type) ring-openings of the intermediate epoxides.
Stereoselective synthesis of N-benzyl conduramine F-1, N-benzyl ent-conduramine E-1, dihydroconduramine F-1 and ent-dihydroconduramine E-1
Katakam, Ramakrishna,Anugula, Rajender,Macha, Lingamurthy,Batchu, Venkateswara Rao
supporting information, p. 559 - 562 (2017/01/16)
A short and stereoselective synthesis of conduramine F-1 and ent-conduramine E-1 derivatives have been achieved starting from D-mannitol using nucleophilic vinylation on imine. A concise sequence of vinylation at both ends of D-mannitol and followed by RC
Stereoselective synthesis of polyhydroxylated aminocyclohexanes
Ahmad, Sajjad,Thomas, Lynne H.,Sutherland, Andrew
, p. 2801 - 2808 (2011/05/12)
The stereoselective synthesis of a series of di- and tri-hydroxylated aminocyclohexane derivatives has been developed. A one-pot, two step tandem process involving an Overman rearrangement and a ring closing metathesis reaction has been utilised for the asymmetric synthesis of (1S)-1-(2′, 2′,2′-trichloromethylcarbonylamino)cyclohexa-2-ene. Oxidation of this cyclohexene derivative was then studied leading to the preparation of two diol analogues in excellent stereoselectivity. (1S)-1-(2′,2′, 2′-trichloromethylcarbonylamino)cyclohexa-2-ene was then converted to a novel allylic alcohol via a 4,5-dihydro-1,3-oxazole. Functionalisation of this allylic alcohol by Upjohn dihydroxylation conditions or by a directed epoxidation/hydrolysis sequence of reactions allowed the synthesis of two dihydroconduramines in excellent stereoselectivity. The stereochemical assignment of all compounds prepared was confirmed by NOE experiments or X-ray structure determination.
Use of enantiomerically pure 7-azabicyclo[2.2.1]heptan-2-ol as a chiral template for the synthesis of aminocyclitols
Pandey, Ganesh,Tiwari, Keshri Nath,Puranik
supporting information; scheme or table, p. 3611 - 3614 (2009/05/07)
(Chemical Equation Presented) Using enantiopure 7-azabicyclo[2.2.1]heptane- 2-ol, the synthesis of cis- as well as trans-2-aminocyclohexanols, dihydroconduramine E-1, and ent-conduramine F-1 has been described.
Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives
Lysek, Robert,Schuetz, Catherine,Favre, Sylvain,O'Sullivan, Anthony C.,Pillonel, Christian,Kruelle, Thomas,Jung, Pierre M.J.,Clotet-Codina, Imma,Este, Jose A.,Vogel, Pierre
, p. 6255 - 6282 (2007/10/03)
A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (±)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward α-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.
(1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation
Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
, p. 2788 - 2811 (2007/10/03)
(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases
Stereospecific synthesis of aminocyclitols via cycloadditions of unsymmetrical, optically pure dienes: Conduramine A-1 and Dihydroconduramine A-1
Hudlicky,Olivo
, p. 6077 - 6080 (2007/10/02)
Stereospecific synthesis of Conduramine A-1 and Dihydroconduramine A-1 has been achieved by a fully regio- and stereospecific hetero Diels-Alder cycloaddition of a nitrosyl derivative and homochiral 1-halocyclohexadiene diols obtained by microbial oxidati
Biocatalysis as the Strategy of Choice in the Exhaustive Enantiomerically Controlled Synthesis of Conduritols
Hudlicky, Tomas,Luna, Hector,Olivo, Horacio F.,Andersen, Catherine,Nugent, Thomas,Price, John D.
, p. 2907 - 2918 (2007/10/02)
An approach to several conduritols, both naturally occurring and unnatural derivatives, is described.The key strategy of this potentially exhaustive approach relies on the bio-oxidation of chloro- or bromo-benzene to their corresponding cis-diols.Subseque
Asymmetric Synthesis of cis-1,3-Diamino-1,3-dideoxycyclitols
Schuerrle, Karsten,Beier, Barbara,Piepersberg, Wolfgang
, p. 2407 - 2412 (2007/10/02)
Starting with the hetero-Diels-Alder reaction of the O-isopropylidene-protected cis-cyclohexa-3,5-diene-1,2-diol with (-)-2,3:5,6-di-O-isopropylidene-1-nitroso-α-D-manno-furanosyl chloride the optically pure (+)-endo-adduct was exclusively formed.After re
