Asymmetric Construction of Rings A-D of Daphnicyclidin-type Alkaloids

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2009 Nov 13

PMID 19904991

Citations 10

Authors

Travis B Dunn

J Michael Ellis

Christiane C Kofink

James R Manning

Larry E Overman

Affiliations

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Abstract

The aza-Cope-Mannich reaction and ring-closing metathesis are key steps in the assembly of intermediates containing rings A-D of Daphniphyllum alkaloids of the daphnicyclidin type such as daphnipaxinin and oldhamine A.

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References

Krasovskiy A, Kopp F, Knochel P . Soluble lanthanide salts (LnCl3.2LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds. Angew Chem Int Ed Engl. 2006; 45(3):497-500. DOI: 10.1002/anie.200502485. View

Kobayashi J, Inaba Y, Shiro M, Yoshida N, Morita H . Daphnicyclidins A-H, novel hexa- or pentacyclic alkaloids from two species of Daphniphyllum. J Am Chem Soc. 2001; 123(46):11402-8. DOI: 10.1021/ja016955e. View

Furstner A . Carbonminus signCarbon Bond Formations Involving Organochromium(III) Reagents. Chem Rev. 2002; 99(4):991-1046. DOI: 10.1021/cr9703360. View

Biswas K, Prieto O, Goldsmith P, Woodward S . Remarkably stable (Me3Al)2DABCO and stereoselective nickel-catalyzed AlR3 (R=Me, Et) additions to aldehydes. Angew Chem Int Ed Engl. 2005; 44(15):2232-4. DOI: 10.1002/anie.200462569. View

Kobayashi J, Kubota T . The Daphniphyllum alkaloids. Nat Prod Rep. 2009; 26(7):936-62. DOI: 10.1039/b813006j. View

Overman L . Molecular Rearrangements in the Construction of Complex Molecules. Tetrahedron. 2010; 65(33):6432-6446. PMC: 2902795. DOI: 10.1016/j.tet.2009.05.067. View

Trost B, Waser J, Meyer A . Total synthesis of (-)-pseudolaric acid B. J Am Chem Soc. 2008; 130(48):16424-34. PMC: 2698933. DOI: 10.1021/ja806724x. View

Ikeda S, Shibuya M, Kanoh N, Iwabuchi Y . Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system. Org Lett. 2009; 11(8):1833-6. DOI: 10.1021/ol9003405. View

Scholl M, Ding S, Lee C, Grubbs R . Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org Lett. 2000; 1(6):953-6. DOI: 10.1021/ol990909q. View

10.

Yang S, Yue J . First diamino Daphniphyllum alkaloid, daphnipaxinin, with an unprecedented heterohexacyclic skeleton from Daphniphyllum paxianum. Org Lett. 2004; 6(9):1401-4. DOI: 10.1021/ol049756j. View

11.

Dudley G, Danishefsky S . A four-step synthesis of the hydroazulene core of guanacastepene. Org Lett. 2001; 3(15):2399-402. DOI: 10.1021/ol016222z. View

12.

Gan X, Bai H, Chen Q, Ma L, Hu L . A zwitterionic alkaloid, containing a rare cyclopentadienyl anion unit, from the stem barks of Daphniphyllum macropodum Miq. Chem Biodivers. 2006; 3(11):1255-9. DOI: 10.1002/cbdv.200690127. View