Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(14): 1953-1955
DOI: 10.1055/s-2002-34382
DOI: 10.1055/s-2002-34382
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Novel Route to Iridoids: Enantioselective Syntheses of Isoiridomyrmecin and α-Skytanthine
Further Information
Received
14 June 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200214SpecialIssue/lookinside/thumbnails/10.1055-s-2002-34382-1.jpg)
Abstract
Enantio- and diastereoselective syntheses of the iridoids (-)-isoiridomyrmecin and (+)-α-skytanthine from a common intermediate (6-bromo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one) were achieved. Key steps in both syntheses are conjugated nucleophilic substitutions (SN2′ anti-reactions) with C1 zinc cyanocuprates.
Key words
enantioselective synthesis - cuprates - natural products - zinc - alkaloids
-
2a Surveys
of previous syntheses of 1a:
Nangia A.Prasuna G.Rao PB. Tetrahedron 1997, 53: 14507 -
2b Surveys of previous syntheses
of 2a:
Franzyk H. In Progress in the Chemistry of Organic Natural Products Vol. 79: Springer; Wien: 2000. p.1 -
3a
Sennhenn P.Gabler B.Helmchen G. Tetrahedron Lett. 1994, 35: 8595 -
3b
Kudis S.Helmchen G. Tetrahedron 1998, 54: 10449 - 4
Corey EJ.Eckrich TM. Tetrahedron Lett. 1983, 24: 3165 -
5a
Chapleo CB.Finch MA.Lee TV.Roberts SM.Newton R. J. Chem. Soc., Perkin Trans 1 1980, 2084 -
5b
Newton RF.Reynolds DP.Davies J.Kay PB.Roberts SM.Wallace TW. J. Chem. Soc., Perkin Trans. 1 1983, 683 -
6a
Marschner C.Baumgartner J.Griengl H. J. Org. Chem. 1995, 60: 5224 -
6b
Johansen SK.Kornø HT.Lundt I. Synthesis 1999, 171 -
6c
Johansen SK.Lundt I. J. Chem. Soc., Perkin Trans. 1 1999, 3615 - 7
Curran DP.Chen M.-H.Leszczweski D.Elliott RL.Rakiewicz DM. J. Org. Chem. 1986, 51: 1612 - 8
Cavill GWK.Locksley HD. Aust. J. Chem. 1957, 352 - 10
Grieco PA.Srinivasan CV. J. Org. Chem. 1981, 46: 2591 -
11a
Casinovi CG.Monache FD.Marini-Bettolo GB.Bianchi E.Garbarono JA. Gazz. Chim. Ital. 1962, 62: 479 -
11b
Eisenbraun EJ.Bright A.Appel HH. Chem. Ind. (London) 1962, 1242 - 12
Knochel P.Chou T.-S.Jubert C.Rajgopal D. J. Org. Chem. 1993, 58: 588 - 14
Knochel P.Rozema MJ.Tucker CE. In Organocopper ReagentsTaylor RJK. Oxford University Press; Oxford: 1994. p.85
References
Ernst, M.; Helmchen, G. submitted.
9This sequence of reactions was carried out with racemic compounds.
13According to control experiments, phthalimide was formed during the preparation of the organozinc compound.