177971-34-5Relevant academic research and scientific papers
Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues
Bringmann, Gerhard,Gulder, Tanja,Hertlein, Barbara,Hemberger, Yasmin,Meyer, Frank
supporting information; experimental part, p. 1151 - 1158 (2010/04/01)
The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids will now facilitate the preparation of structural analogues for structure-activity relationship studies. Its general applicability was shown by the preparation of the sterically even more congested, as yet unnatural N,3′- and N,1′-coupled analogues, ancistrocladinium C (5) and D (6).
Total synthesis of michellamines A-C, korupensamines A-D, and ancistrobrevine B
Hoye, Thomas R.,Chen, Minzhang,Hoang, Bac,Mi, Liang,Priest, Owen P.
, p. 7184 - 7201 (2007/10/03)
Efficient syntheses of the title compounds have been developed. Several strategies for preparation of each of the naphthalene and tetrahydroisoquinoline (THIQ) portions were developed. Initial attempts to use benzyne plus furan cycloaddition reactions wer
Total synthesis of (ent)-korupensamine D
Hoye, Thomas R.,Chen, Minzhang
, p. 3099 - 3100 (2007/10/03)
The first total synthesis of the enantiomer of the natural product, korupensamine D (16R), is described. The key steps include a highly efficient preparation of the enantiomerically pure primary amine 4 via the ring opening of aziridine 2 with an arylcupr
TOTAL SYNTHESIS OF MICHELLAMINES A-C: IMPORTANT ANTI-HIV AGENTS
Hoye, Thomas R.,Chen, Minzhang,Mi, Liang,Priest, Owen P.
, p. 8747 - 8750 (2007/10/02)
Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively.Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2'-binaphthol.
