156714-46-4Relevant articles and documents
The search for new odorants: Synthesis of animalic fragrant and musky/ambery compounds
Plessis, Caroline
, p. 1517 - 1539 (2015/03/03)
An overview of the recent research which allowed us to discover novel animalic odorants is presented. The new derivatives were prepared from readily available starting materials via easy reaction steps in good yields. They possess very different structures, such as bicyclic pentanols, glycolates, or tricyclic ketones, and all show interesting notes in the animalic fragrant family: from costus, leathery to ambery and musky scents, making them all attractive for different purposes.
Total synthesis of (+)-chinensiolide B via tandem allylboration/ lactonization
Elford, Tim G.,Hall, Dennis G.
scheme or table, p. 1488 - 1489 (2010/04/04)
(Chemical Equation Presented) The chinensiolides are a family of guaiane type α-methylene γ-lactone natural products recently isolated from Ixeris chinensis Nakai, a plant used in Chinese folk medicine. The first enantioselective total synthesis of (+)-chinensiolide B was accomplished in 15 steps for the longest linear sequence with an overall yield of 6.7% starting from inexpensive and readily available (R)-carvone. A highly stereoselective and E/Z-selective tandem allylboration/lactonization reaction between two highly functionalized partners was exploited as a key step. The synthesis also highlights several solutions to chemoselectivity issues arising from the reactive α-methylene γ-lactone. For instance, a ring-closing metathesis formed the requisite seven-membered ring in a chemoselective fashion while avoiding the reactivity of the conjugated α-methylene unit.
Total synthesis of (-)-incarvilline and (-)-incarvillateine
Zhang, Fengying,Jia, Yanxing
scheme or table, p. 6840 - 6843 (2009/12/06)
An enantioselective, concise total synthesis of (-)-incarvilline and (-)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (-)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorohydrin derivative of (-)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with α-truxillic acid anhydride to generate incarvillateine skeleton.
Opening of epoxide rings catalyzed by niobium pentachloride
Constantino, Mauricio Gomes,Lacerda Jr., Valdemar,Invernize, Paulo Roberto,Filho, Luiz Carlos Da Silva,Da Silva, Gil Valdo Jose
, p. 3529 - 3539 (2008/03/13)
The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or -78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions. Copyright Taylor & Francis Group, LLC.
Stereoselective Favorskii Rearrangement of Carvone Chlorohydrin; Expedient Synthesis of (+)-Dihydronepetalactone and (+)-Iridomyrmecin
Lee, Eun,Yoon, Cheol Hwan
, p. 479 - 482 (2007/10/02)
(+)-Dihydronepetalactone and (+)-iridomyrmecin were synthesized from the stereoselective Favorskii rearrangement product of (+)-carvone chlorohydrin.
