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Literature DB >> 19957923

An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.

Thomas J A Graham¹, Erin E Gray, James M Burgess, Brian C Goess.

Abstract

An eight-step synthesis of (+/-)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate conversion correlated strongly with the identity of the ligands on the catalyst. In addition, new reactivity of 1-alkenylcyclobutenes toward hydrogenation is described.

Entities: Chemical Disease Species

Mesh：

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Year: 2010 PMID： 19957923 PMCID： PMC2798917 DOI： 10.1021/jo9020375

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

4 in total

1. A Concise Total Synthesis of Dactylol via Ring Closing Metathesis.

Authors: Alois Fürstner; Klaus Langemann
Journal: J Org Chem Date: 1996-12-13 Impact factor: 4.354

2. 1,5-Enyne metathesis.

Authors: Olivier Debleds; Jean-Marc Campagne
Journal: J Am Chem Soc Date: 2008-01-12 Impact factor: 15.419

3. Total synthesis of (+/-)-chartelline C.

Authors: Phil S Baran; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

4. Enantiomeric composition of grandisol and grandisal produced byPissodes strobi andP. nemorensis and their electroantennogram response to pure enantiomers.

Authors: B E Hibbard; F X Webster
Journal: J Chem Ecol Date: 1993-10 Impact factor: 2.626

4 in total

An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.

1. A Concise Total Synthesis of Dactylol via Ring Closing Metathesis.

2. 1,5-Enyne metathesis.

3. Total synthesis of (+/-)-chartelline C.

4. Enantiomeric composition of grandisol and grandisal produced byPissodes strobi andP. nemorensis and their electroantennogram response to pure enantiomers.

1. Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

2. Gold-catalyzed propargylic substitutions: Scope and synthetic developments.

3. Essential Oil Biodiversity of Achillea ligustica All. Obtained from Mainland and Island Populations.

4. A cross-metathesis approach to novel pantothenamide derivatives.