Synthesis of spongistatin 2 employing a new route to the EF fragment

Helmut Kraus; Antoine Français; Matthew O'Brien; James Frost; Alejandro Diéguez-Vázquez; Alessandra Polara; Nikla Baricordi; Richard Horan; Day-Shin Hsu; Takashi Tsunoda; Steven V. Ley

doi:10.1039/C3SC50304F

Synthesis of spongistatin 2 employing a new route to the EF fragment†

Helmut Kraus,^a Antoine Français,^a Matthew O'Brien,^ab James Frost,^a Alejandro Diéguez-Vázquez,^a Alessandra Polara,^a Nikla Baricordi,^a Richard Horan,^a Day-Shin Hsu,^a Takashi Tsunoda^a and Steven V. Ley*^a

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^a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 (0)1223 336442
Tel: +44 (0)1223 336398

^b Lennard-Jones Laboratories, Keele University, Keele, Staffordshire, UK
E-mail: m.obrien@keele.ac.uk
Tel: +44 (0)1782 734371

Abstract

An improved route to the EF fragment of the spongistatins has been developed and employed in a synthesis of spongistatin 2. The C48–C51 diene side chain, which lacks the chlorine substituent present in spongistatin 1, presented some compatibility issues during target assembly. These were overcome by implementing a late stage Stille cross coupling to construct the diene portion of the natural product.

Chemical Science

Synthesis of spongistatin 2 employing a new route to the EF fragment†

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Synthesis of spongistatin 2 employing a new route to the EF fragment

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