Enantioselective Approach to the Right-Hand Substructure of Solanoeclepin A

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Title:	Enantioselective Approach to the Right-Hand Substructure of Solanoeclepin A
Author(s):	Lutteke, G.; Kleinnijenhuis, R.A.; Beuving, R.J.; de Gelder, René ; Smits, J.M.M.; van Maarseveen, J.H.; Hiemstra, H.
Publication year:	2016
Source:	European Journal of Organic Chemistry, iss. 35, (2016), pp. 5845-5854
ISSN:	1434-193X
DOI:	http://dx.doi.org/10.1002/ejoc.201601094
Publication type:	Article / Letter to editor
Please use this identifier to cite or link to this item : http://hdl.handle.net/2066/166213
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Subject:	Solid State Chemistry
Organization:	Solid State Chemistry
Journal title:	European Journal of Organic Chemistry
Issue:	iss. 35
Page start:	p. 5845
Page end:	p. 5854
Abstract:	An enantioselective synthesis of the right-hand substructure of solanoeclepin A has been developed. The key step was an intramolecular [2+2] photocycloaddition between an allene and a butenolide providing a methylenecyclobutane with three quaternary carbon atoms in a complex tetracyclic framework. Other crucial steps included an enantioselective Noyori transfer hydrogenation of a ketone, a diastereoselective silver-mediated silyl dienolate allylation, and a diastereoselective cyclopropanation of an allylic alcohol. The installation of the bridgehead methyl group by reduction of the lactone moiety proved to be troublesome.