Using (R)-propene oxide as a chiral building block a convergent enantioselective synthesis of the potent neuronal cell protecting alkaloid lavanduquinocin has been accomplished by the iron-mediated one-pot construction of the carbazole framework. Chirality 12:526–528, 2000. © 2000 Wiley-Liss, Inc.

LITERATURE CITED

1Part 58: Knölker H-J, Baum E, Reddy KR. First enantioselective total synthesis of the potent neuronal cell protecting substance carquinostatin A from (R)-propene oxide. Tetrahedron Lett 2000; 41: 1171–1174.
10.1016/S0040-4039(99)02257-1
CAS Web of Science® Google Scholar
2Chakraborty DP. Chemistry and biology of carbazole alkaloids. In: GA Cordell, editor. The alkaloids, vol. 44. New York: Academic Press; 1993. p 257–364.
Google Scholar
3Furukawa H. Carbazolequinone alkaloids. J Indian Chem Soc 1994; 71: 303–308.
CAS Web of Science® Google Scholar
4Shin-ya K, Tanaka M, Furihata K, Hayakawa Y, Seto H. Structure of carquinostatin A, a new neuronal cell protecting substance produced by Streptomyces exfoliatus. Tetrahedron Lett 1993; 34: 4943–4944.
10.1016/S0040-4039(00)74052-4
CAS Web of Science® Google Scholar
5Tanaka M, Shin-ya K, Furihata K, Seto H. Isolation and structural elucidation of antioxidative substances, carbazoquinocins A to F. J Antibiot 1995; 48: 326–328.
10.7164/antibiotics.48.326
CAS PubMed Web of Science® Google Scholar
6Shin-ya K, Shimizu S, Kunigami T, Furihata K, Furihata K, Seto H. A new neuronal cell protecting substance, lavanduquinocin, produced by Streptomyces viridochromogenes. J Antibiot 1995; 48: 574–578.
10.7164/antibiotics.48.574
CAS PubMed Web of Science® Google Scholar
7Knölker H-J. Organic synthesis via tricarbonyl(η⁴-diene)iron complexes. Chem Soc Rev 1999; 28: 151–157.
10.1039/a705401g
CAS Web of Science® Google Scholar
8Knölker H-J, Fröhner W. First total synthesis of the potent neuronal cell protecting substance (±)-lavanduquinocin via iron- and nickel-mediated coupling reactions. Tetrahedron Lett 1998; 39: 2537–2540.
10.1016/S0040-4039(98)00340-2
CAS Web of Science® Google Scholar
9Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN. Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. Science 1997; 277: 936–938.
10.1126/science.277.5328.936
CAS PubMed Web of Science® Google Scholar
10Schaus SE, Branalt J, Jacobsen EN. Total synthesis of muconin by efficient assembly of chiral building blocks. J Org Chem 1998; 63: 4876–4877.
10.1021/jo9810765
CAS Web of Science® Google Scholar
11Albrecht M. Synthesis of linear oligo(catechol) ligands for the metal directed self-assembling of helicates. Synthesis 1996; 230–236.
10.1055/s-1996-4188
CAS Web of Science® Google Scholar
12Knölker H-J, Fröhner W. Convergent iron-mediated total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C. Tetrahedron Lett 1997; 38: 1535–1538.
10.1016/S0040-4039(97)00114-7
Web of Science® Google Scholar
13Knölker H-J, Baum G, Pannek J-B. Synthesis and reactivity of 4a,9a-dihydro-9H-carbazoles. Tetrahedron 1996; 52: 7345–7362.
10.1016/0040-4020(96)00256-6
Web of Science® Google Scholar
14Shvo Y, Hazum E. A simple method for the disengagement of organic ligands from iron complexes. J Chem Soc Chem Commun 1974; 336–337.
10.1039/c39740000336
CAS Web of Science® Google Scholar
15Flack HD. On enantiomorph-polarity estimation. Acta Crystallogr Sect A 1983; 39: 876–881.
10.1107/S0108767383001762
CAS Web of Science® Google Scholar
16Billington DC. π-Allylnickel halides as selective reagents in organic synthesis. Chem Soc Rev 1985; 14: 93–120.
10.1039/cs9851400093
CAS Web of Science® Google Scholar
17Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973; 95: 512–519.
10.1021/ja00783a034
CAS Web of Science® Google Scholar

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Volume12, Issue5-6

SPECIAL COMMEMORATIVE ISSUE HONORING PROFESSOR RYOJI NOYORI

2000

Pages 526-528

Transition metal complexes in organic synthesis, part 59.¹ First enantioselective total synthesis of lavanduquinocin, a potent neuronal cell protecting substance from Streptomyces viridochromogenes

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Transition metal complexes in organic synthesis, part 59.1 First enantioselective total synthesis of lavanduquinocin, a potent neuronal cell protecting substance from Streptomyces viridochromogenes

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Transition metal complexes in organic synthesis, part 59.¹ First enantioselective total synthesis of lavanduquinocin, a potent neuronal cell protecting substance from Streptomyces viridochromogenes