Synthesis of the all-cis-trimethyldecalin fragment of unusual terpenes by radical-mediated protonolysis of an alkylboron derivative

Autor:	Ben Bradshaw, Josep Bonjoch, Giorgio Villa, Philippe Renaud, Cédric Bürki
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Ketone Double bond Stereochemistry Organic Chemistry Biochemistry Disiamylborane chemistry.chemical_compound Hydroboration Enantiopure drug chemistry Drug Discovery Protonolysis Methylene Derivative (chemistry)
Zdroj:	Tetrahedron Letters. 55:4608-4611
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.06.075
Popis:	The synthesis of an enantiopure building-block with a contiguous all-cis-trimethyldecalin motif embedded in unusual terpenes is described. Starting from the Wieland–Miescher ketone, the key step is a one-pot hydroboration of an exocyclic methylene double bond promoted by disiamylborane and radical-mediated protonolysis of the corresponding alkylborane using 4-tert-butylcatechol.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d21d6dcc3dd1955d8a8ceef27b3bf425 https://doi.org/10.1016/j.tetlet.2014.06.075 Zobrazit plný text záznamu Full Text from ScienceDirect