157752-14-2Relevant 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.
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.
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.