Stereoselective total synthesis of garsubellin A

Journal of Antibiotics

Volumn 66, Issue 3, 2013, Pages 141-145

  Uwamori, Masahiro ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

cyclopropanation; garsubellin A; natural product; stereoselective synthesis; total synthesis

Indexed keywords

BICYCLO[3.3.1]NONANE DERIVATIVE; GARSUBELLIN A; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ALLYLATION; ARTICLE; BIRCH REDUCTION; CARBONYLATION; CYCLOPROPANATION; DESS MARTIN OXIDATION; DIHYDROXYLATION; DRUG SYNTHESIS; EPOXIDATION; HYDROGENATION; METHYLATION; OPPENAUER OXIDATION; PRENYLATION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

BIOLOGICAL AGENTS; CHOLINE O-ACETYLTRANSFERASE; CYCLOPROPANES; STEREOISOMERISM; TERPENES;

EID: 84875728802     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2012.125     Document Type: Article

References (19)

1. Numbering of compounds corresponds to Fukuyama's report, see: Fukuyama, Y., Kuwayama, A. & Minami, H. Garsubellin A, a novel polyprenylated phloroglucin derivative, increasing choline acetyltransferase (ChAT) activity in postnatal rat septal neuron cultures. Chem. Pharm. Bull 45, 947-949 (1997).
2. Njardarson, J. T. Synthetic efforts toward [3.3.1] bridged bicyclic phloroglucinol natural products. Tetrahedron 67, 7631-7666 (2011).
3. Richard, J. A., Pouwer, R. H. & Chen, D. Y. -K. The chemistry of the polycyclic polyprenylated acylphloroglucinols. Angew. Chem. Int. Ed. 51, 4536-4561 (2012).
4. Kuramochi, A., Usuda, H., Yamatsugu, K., Kanai, M. & Shibasaki, M. Total synthesis of (±)-garsubellin A. J. Am. Chem. Soc. 127, 14200-14201 (2005).
5. Siegel, D. R. & Danishefsky, S. J. Total synthesis of garsubellin A. J. Am. Chem. Soc. 128, 1048-1049 (2006).
6. Ahmad, N. M., Rodeschini, V., Simpkins, N. S., Ward, S. E. & Blake, A. J. Synthesis of polyprenylated acylphloroglucinols using bridgehead lithiation: total synthesis of racemic clusianone and a formal synthesis of racemic garsubellin A. J. Org. Chem. 72, 4803-4815 (2007).
7. Ciochina, R. & Grossman, R. B. Polycyclic polyprenylated acylphloroglucinols. Chem. Rev. 106, 3963-3986 (2006).
8. Bystrov, N. S., Chernov, B. K., Dobrynin, V. N. & Kolosov, M. N. The structure of hyperforin. Tetrahedron. Lett. 16, 2791-2794 (1975).
9. Cuesta-Rubio, O., Frontana-Uribe, B. A., Ramírez-Apan, T. & Cárdenas, J. Z. Polyisoprenylated benzophenones in cuban propolis; biological activity of nemorosone. Naturforsch. C 57, 372-378 (2002).
10. Uwamori, M., Saito, A. & Nakada, M. Stereoselective total synthesis of nemorosone. J. Org. Chem. 77, 5098-5107 (2012).
11. Honma, M. et al. Asymmetric catalysis on the intramolecular cyclopropanations of a-diazo-b-keto sulfones. J. Am. Chem. Soc. 125, 2860-2861 (2003).
12. Honma, M., Takeda, H., Takano, M. & Nakada, M. Development of catalytic asymmetric intramolecular cyclopropanation for a-diazo-b-keto sulfones and applications to natural product synthesis. Synlett 1695-1712 (2009).
13. Ashby, E. C. & Noding, S. A. Alkylation of enones and ketones using substituted alkyland arylaluminum compounds. J. Org. Chem. 44, 4792-4797 (1979).
14. Graves, C. R., Zeng, B.-S. & Nguyen, S. T. Efficient and selective Al-catalyzed alcohol oxidation via Oppenauer chemistry. J. Am. Chem. Soc. 128, 12596-12597 (2006).
15. Crabtree, R. H. et al. Dihydrido olefin and solvent complexes of iridium and the mechanisms of olefin hydrogenation and alkane dehydrogenation. J. Am. Chem. Soc. 104, 6994-7001 (1982).
16. Yu, J-Q. & Corey, E. J. A mild, catalytic, and highly selective method for the oxidation of a, b-enones to 1,4-enediones. J. Am. Chem. Soc. 125, 3232-3233 (2003).
17. Lipshutz, B. H., Koerner, M. & Parker, D. A. 2-Thienyl(cyano)copper lithium. a lower order, stable ''cuprate in a bottle'' precursor to higher order reagents. Tetrahedron. Lett. 28, 945-948 (1987).
18. Krasovskiy, A., Kopp, F. & Knochel, P. Soluble lanthanide salts (LnCl32LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds. Angew. Chem. Int. Ed. 45, 497-500 (2006).
19. Chatterjee, A. K., Sanders, D. P. & Grubbs, R. H. Synthesis of symmetrical trisubstituted olefins by cross metathesis. Org. Lett. 4, 1939-1942 (2002).