Synthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction

A practical synthesis of a novel oxabicyclo[6.2.1]undecenetriol useful as a medicinal chemistry scaffold has been developed starting from l‐ribose. The sequence involves an oxidation/Grignard addition sequence and a challenging ring‐closing metathesis (RCM) reaction as the ring forming step. Explora...

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Vydané v:	European journal of organic chemistry Ročník 2016; číslo 26; s. 4496 - 4507
Hlavní autori:	Rankin, Stuart S., Caldwell, John J., Cronin, Nora B., van Montfort, Rob L. M., Collins, Ian
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	WEINHEIM Blackwell Publishing Ltd 01.09.2016 Wiley Wiley Subscription Services, Inc John Wiley and Sons Inc
Predmet:	Carbohydrates Chemistry Chemistry, Organic Cyclization Fused-ring systems Medium-ring compounds Metathesis Physical Sciences Science & Technology Carbohydrates ETHERS Cyclization HETEROCYCLES LACTONES ANALOGS Metathesis Medium-ring compounds OLEFIN METATHESIS PRECURSORS Fused-ring systems CATALYSTS Fused‐ring systems Medium‐ring compounds
ISSN:	1434-193X, 1099-0690
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Shrnutí:	A practical synthesis of a novel oxabicyclo[6.2.1]undecenetriol useful as a medicinal chemistry scaffold has been developed starting from l‐ribose. The sequence involves an oxidation/Grignard addition sequence and a challenging ring‐closing metathesis (RCM) reaction as the ring forming step. Exploration of the RCM substrate protecting groups revealed the key factor for successful nine‐membered medium ring formation to be conformational bias of the reacting alkenes of the RCM substrate by very bulky silyl ether protecting groups. The synthesis also allowed access to an epimeric triol and saturated and unsaturated variants of the nine‐membered ring. The medium ring conformation of the oxabicyclo[6.2.1]undecenetriol was determined by X‐ray crystallography and correlated to the solution state conformation by NMR experiments. A practical synthesis of a novel oxabicyclo[6.2.1]undecenetriol has been developed, via a challenging ring‐closing metathesis (RCM) reaction. The key factor for successful medium ring formation was the use of bulky silyl ether protecting groups. X‐ray crystallography of the triol and NMR experiments revealed a well‐defined medium ring conformation.
Bibliografia:	istex:2828ECDCF64930252652EEA916CA79D6FC53D41D Cancer Research UK - No. C309/A11566 ArticleID:EJOC201600756 The Institute of Cancer Research ark:/67375/WNG-8CB216C3-D Wellcome Trust - No. 099766/Z/12 Supporting Information ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.201600756