Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

Jorg C. J. Benningshof; Richard H. Blaauw; Angeline E. van Ginkel; Floris P. J. T. Rutjes; Jan Fraanje; Kees Goubitz; Henk Schenk; Henk Hiemstra

doi:10.1039/B003757P

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Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

Jorg C. J. Benningshof,^a Richard H. Blaauw,^a Angeline E. van Ginkel,^a Floris P. J. T. Rutjes,^a Jan Fraanje,†^a Kees Goubitz,†^a Henk Schenk †^a and Henk Hiemstra*^a

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* Corresponding authors

^a Institute of Molecular Chemistry, Laboratories of Organic Chemistry and Crystallography, University of Amsterdam, Nieuwe Achtergracht 129, Amsterdam, The Netherlands.
E-mail: henkh@org.chem.uva.nl

Abstract

The synthesis of the enantiopure left-hand substructure of solanoeclepin A is described. Key steps include a chromium-mediated coupling of an oxabicyclic aldehyde with a β-ketoester-derived enol triflate to give a lactone, and a ring-closing metathesis reaction to form the seven-membered ring.

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Supplementary files

Crystal structure data TXT (59K)

Article information

DOI: https://doi.org/10.1039/B003757P
Article type: Communication
Submitted: 09 May 2000
Accepted: 20 Jun 2000
First published: 14 Jul 2000

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Chem. Commun., 2000, 1465-1466

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Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

J. C. J. Benningshof, R. H. Blaauw, A. E. van Ginkel, F. P. J. T. Rutjes, J. Fraanje, K. Goubitz, H. Schenk and H. Hiemstra, Chem. Commun., 2000, 1465 DOI: 10.1039/B003757P

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Chemical Communications

Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

Abstract

Supplementary files

Article information

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Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

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