• Title/Summary/Keyword: Enantioselective total synthesis

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Enantioselective Total Synthesis of (-)-Clavosolide A and B

  • Son, Jung-Beom;Kim, Si-Nae;Kim, Na-Yeong;Hwang, Min-Ho;Lee, Won-Sun;Lee, Duck-Hyung
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.653-663
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    • 2010
  • Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and $^1H$ and $^{13}C$ NMR spectra of them.

Studies on the Synthesis of Naphthoquinoids-1 : Formal Total Synthesis of (+)-6-Oxo-3,4,4a,5-tetra hydro-3-hydroxy-2,2-dimethylnaphtho-1,2-pyran

  • Park, Oee-Sook;Lim, Jae-Gyeong
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.581-585
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    • 1996
  • A new formal total synthesis of (+)-6-oxo-3, 4, 4a, 5-tetrahydro-3-hydroxy-2, 2-dimenthylnaphtho-1, 2-pyran (1) which has been known to have bactericidal, bacteriostatic, fungicidal, fungistatic activities against Staphylococcus aureus and other microorganism, is described. The key reaction involves enantioselective prenylation of .alpha.-tetralone via chiral lithioenamine.

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First Total Synthesis of (-)-Antofine by Using Catalytic Phase Transfer Alkylation.

  • Lee, Jae-Kwang;Lee, Tae-Ho;Park, Hyeung-Geun;Kim, Deuk-Joon;Kim, Sang-Hee
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.183.3-183.3
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    • 2003
  • Phenanthroindolizidine alkaloid, (-)-antofine has attracted attention because of its extremely potent inhibition of cancer cell growth (Its $IC_50$ values have the low nanomolar range). The frist asymmetric total synthesis of (-)-antofine is described. An important feature of this synthesis is the creation of a stereogenic center by enantioselective alkylation using the phase transfer catalyst (PTC) and ring-closing metathesis (RCM) for pyrrolidine ring construction. This synthesis is efficient to allow the asymmetric preparation of other naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloid.

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