156629-17-3Relevant articles and documents
Synthesis of the guaianolide ring system via cycloaddition of a bicyclic carbonyl ylide with allyl propiolate
Navickas, Vaidotas,Ushakov, Dmitry B.,Maier, Martin E.,Stroebele, Markus,Meyer, H.-Juergen
, p. 3418 - 3421 (2010)
(Equation Presented). A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh2(OAc)4-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation, the cycloadduct was transformed to the ring skeleton typical of the sesquiterpene family of guaianolides.
Stereoselective Favorskii Rearrangement of Carvone Chlorohydrin; Expedient Synthesis of (+)-Dihydronepetalactone and (+)-Iridomyrmecin
Lee, Eun,Yoon, Cheol Hwan
, p. 479 - 482 (1994)
(+)-Dihydronepetalactone and (+)-iridomyrmecin were synthesized from the stereoselective Favorskii rearrangement product of (+)-carvone chlorohydrin.
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 (-)-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.
