155239-06-8Relevant articles and documents
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.
Efficient enantiospecific synthesis of ent-conduramine F-1
Prasad, Kavirayani R.,Rangari, Vipin Ashok
, p. 6689 - 6693 (2018/10/15)
An efficient enantiospecific total synthesis of ent-conduramine F-1 (aminocyclohexenetriol) was accomplished starting from the bis-Weinreb amide of tartaric acid. Key reactions in the synthesis include the desymmetrization of tartaric acid amide with viny
Asymmetric total synthesis of (?)-conduramine A-1 via a chiral syn,anti-oxazine
Myeong, In-Soo,Kim, Jin-Seok,Lee, Yong-Taek,Kang, Jong-Cheol,Park, Seok-Hwi,Jung, Changyoung,Ham, Won-Hun
, p. 823 - 828 (2016/09/02)
The total synthesis of (?)-conduramine A-1 was achieved by using a diastereomerically enriched syn,anti-oxazine intermediate. The key steps in this strategy were the stereoselective extension of the chirality of syn,anti-oxazine, a Wittig reaction, and a ring-closing metathesis reaction.
A Chiron Approach to Diversity-Oriented Synthesis of Aminocyclitols, (-)-Conduramine F-4 and Polyhydroxyaminoazepanes from a Common Precursor
Harit, Vimal Kant,Ramesh, Namakkal G.
, p. 11574 - 11586 (2016/12/09)
The total syntheses of aminocyclitols, (-)-conduramine F-4, and polyhydroxyaminoazepanes have been achieved from a common precursor derived from tri-O-benzyl-d-glucal through a 'diversity-oriented' approach. Tri-O-benzyl-d-glucal was converted into a protected 1,6-diol through a sequence of steps that include transformation to a 2-tosylamidoglucose derivative, selective deprotection of primary C-6 benzyloxy group, LiAlH4-mediated one-step reduction of acetate groups, and reductive ring opening of the resulting hemiacetal as the key steps. The 1,6-diol served as a common precursor in our diversity oriented approach toward the target molecules. Mesylation of the diol followed by double nucleophilic substitution reaction with primary amines led to the synthesis of amino-substituted polyhydroxyazepanes. On the other hand, dialdehyde obtained from the oxidation of 1,6-diol was found to be a convenient starting material for the synthesis of aminocyclitols and (-)-conduramine F-4. McMurry coupling of the dialdehyde was successfully employed, for the first time, to construct the carbocyclic framework of aminoyclitols, while bis-Wittig olefination of the dialdehyde followed by Grubb's(II)-catalyzed RCM delivered (-)-conduramine F-4. The stereochemistry of newly created chiral centers in aminocyclitols was established through single crystal X-ray crystallography and detailed NOE studies.
Dearomative dihydroxylation with arenophiles
Southgate, Emma H.,Pospech, Jola,Fu, Junkai,Holycross, Daniel R.,Sarlah, David
, p. 922 - 928 (2016/09/28)
Aromatic hydrocarbons are some of the most elementary feedstock chemicals, produced annually on a million metric ton scale, and are used in the production of polymers, paints, agrochemicals and pharmaceuticals. Dearomatization reactions convert simple, readily available arenes into more complex molecules with broader potential utility, however, despite substantial progress and achievements in this field, there are relatively few methods for the dearomatization of simple arenes that also selectively introduce functionality. Here we describe a new dearomatization process that involves visible-light activation of small heteroatom-containing organic molecules - arenophiles - that results in their para-cycloaddition with a variety of aromatic compounds. The approach uses N-N-arenophiles to enable dearomative dihydroxylation and diaminodihydroxylation of simple arenes. This strategy provides direct and selective access to highly functionalized cyclohexenes and cyclohexadienes and is orthogonal to existing chemical and biological dearomatization processes. Finally, we demonstrate the synthetic utility of this strategy with the concise synthesis of several biologically active compounds and natural products.
Stereoselective synthesis of (-)-conduramine C-1 and (-)-conduramine D-1
Rajender, Anugula,Rao, Batchu Venkateswara
supporting information, p. 2329 - 2331 (2013/06/27)
A highly stereoselective approach to aminocyclohexenetriols conduramine C-1 1 and conduramine D-1 2 has been described. Conduramines are structural units of some biologically active natural products such as (+)-lycoricidine and (+)-narciclasine. The strategy developed by us for their synthesis is general in nature to make related skeletons and also the molecules containing conduramine structural unit. The key reactions are Grignard addition on glycosylamine, ring closing metathesis (RCM), and Mitsunobu inversion.
Remarkable stereoselectivity in intramolecular Borono-Mannich reactions: Synthesis of conduramines
Norsikian, Stephanie,Soule, Jean-Francois,Cannillo, Alexandre,Guillot, Regis,Tran Huu Dau, Marie-Elise,Beau, Jean-Marie
, p. 544 - 547 (2012/03/26)
An unprecedented intramolecular Petasis condensation provides a novel approach to biologically important conduramines. The compounds are produced with an exclusive anti stereoselectivity for the newly created β-amino alcohol motif. The stereochemical outc
Formal total synthesis of (±)-conduramine E utilising the Bryce-Smith-Gilbert photoamination reaction
Chappell, David,Drew, Michael G.B.,Gibson, Shane,Harwood, Laurence M.,Russell, Andrew T.
body text, p. 517 - 520 (2010/09/11)
Utilising a Bryce-Smith-Gilbert photoamination of benzene as a key step, a synthesis of (±)-conduramine E was carried out. A highly regioselective dihydroxylation of a cyclic diene was effected utilising Sharpless AD-mix-β. Georg Thieme Verlag Stuttgart.
Syntheses of optically pure conduramines via the strategy of hetero diels-alder reaction of masked o -benzoquinones with homochiral nitroso dienophiles
Lu, Ping-Hsun,Yang, Ching-Shun,Devendar, Badugu,Liao, Chun-Chen
supporting information; experimental part, p. 2642 - 2645 (2010/08/22)
Highly stereoselective hetero Diels-Alder reactions of masked o-benzoquinones (MOBs) with homochiral nitroso dienophiles are described along with their application in the syntheses of (+)-ent-conduramine F-1, (+)-conduramine E-1, (-)-conduramine A-1, (+)-
A flexible strategy based on a C2-symmetric pool of chiral substrates: Concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E
Chang, Yuan-Kang,Lo, Hong-Jay,Yan, Tu-Hsin
supporting information; experimental part, p. 4278 - 4281 (2010/01/16)
A new strategy invoking a new application of the [3,3] sigmatropic rearrangement of allylic azides and the presence of a C2 symmetry element within a pool of chiral substrates was evolved. Not only does this simple flexible strategy provide a concise approach to (+)-valienamine, but it also can readily be adopted for the synthesis of conduramines A-1 and E and the enantiopure azido carbonate 4, a key intermediate of (+)-pancratistatin.
