Improved synthesis of (R)-7-hydroxycarvone from (S)-α-pinene

Autor:	Ryosuke Kondo, Yuki Egoshi, Toru Sugiyama, Yukiko Yoshimoto, Toyonobu Usuki
Rok vydání:	2013
Předmět:	Reaction conditions chemistry.chemical_compound Pinene Tetrapropylammonium perruthenate chemistry Yield (chemistry) Organic Chemistry Drug Discovery Organic chemistry Photooxygenation Alcohol Biochemistry (R)-7-hydroxycarvone
Zdroj:	Tetrahedron Letters. 54:7029-7030
ISSN:	0040-4039
Popis:	A three-step synthesis of (R)-7-hydroxycarvone (1), which is anticipated to be a valuable building block for the versatile preparation of natural products, is described. Optimization of the reaction conditions for photooxygenation and migration of (S)-α-pinene 2, tetrapropylammonium perruthenate (TPAP) oxidation of the generated alcohol, and a subsequent ring-opening reaction in the presence of Cu(OTf)2 led to the synthesis of 1 with good reproducibility. The desired product 1 was thus obtained in 46% yield over three steps.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::74ec52209f43665dee4761da7183efe9 https://doi.org/10.1016/j.tetlet.2013.10.066 Zobrazit plný text záznamu Full Text from ScienceDirect