Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction

Ross. P. Wilkie; Andrew R. Neal; Craig A. Johnston; Nicholas Voute; Christopher S. Lancefield; Matthew D. Stell; Federico Medda; Edward F. Makiyi; Emma M. Turner; O. Stephen Ojo; Alexandra M. Z. Slawin; Tomas Lebl; Peter Mullen; David J. Harrison; Chris M. Ireland; Nicholas J. Westwood

doi:10.1039/C6CC05747K

Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction†

Ross. P. Wilkie,‡^a Andrew R. Neal,‡^a Craig A. Johnston,^a Nicholas Voute,^a Christopher S. Lancefield,^a Matthew D. Stell,^a Federico Medda,^a Edward F. Makiyi,^a Emma M. Turner,^a O. Stephen Ojo,^a Alexandra M. Z. Slawin,^a Tomas Lebl,^a Peter Mullen,^b David J. Harrison,^b Chris M. Ireland^c and Nicholas J. Westwood

*^a

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* Corresponding authors

^a School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, St. Andrews, Fife, Scotland, UK
E-mail: njw3@st-andrews.ac.uk

^b School of Medicine, University of St Andrews, St. Andrews, Fife, Scotland, UK

^c Department of Medicinal Chemistry, University of Utah, 30 South 2000 East, Salt Lake City, UT 84112, USA

Abstract

The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.

Chemical Communications

Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction†

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Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction

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