302840-41-1Relevant academic research and scientific papers
Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation
Liu, Yiyang,Liniger, Marc,McFadden, Ryan M.,Roizen, Jenny L.,Malette, Jacquie,Reeves, Corey M.,Behenna, Douglas C.,Seto, Masaki,Kim, Jimin,Mohr, Justin T.,Virgil, Scott C.,Stoltz, Brian M.
, p. 2501 - 2512 (2015/02/19)
Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of "classic" natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.
Enantiospecific total synthesis of ent-5-senecioyloxy-10,11-epoxythapsan- 10-ol
Srikrishna,Anebouselvy
scheme or table, p. 776 - 788 (2011/01/04)
Enantiospecific total synthesis of optical antipode of the sesquiterpene 5-senecioyloxy-10,11-epoxythapsan-10-ol has been described. (R)-Carvone has been employed as the chiral starting material and a combination of intramolecular alkyation and Criegee fr
Enantiospecific total synthesis of ent-10,1 l-thapsan-10-ol
Srikrishna,Anebouselvy
scheme or table, p. 413 - 422 (2009/12/24)
First enantiospecific total synthesis of optical antipode of the sesquiterpene 10,1 l-epoxythapsan-10-ol has been described. (R)-Carvone has been employed as the chiral starting material and a combination of intramolecular alkylation and Criegee fragmenta
Enantiospecific synthesis of thaps-8-en-5-ol via stereospecific intramolecular chirality transfer
Srikrishna,Anebouselvy
, p. 449 - 459 (2008/09/20)
Enantiospecific synthesis of thaps-8-en-5-ol, comprising of the carbon framework of a small group of sesquiterpenes containing three contiguous quaternary carbon atoms has been described. (R)-Carvone has been employed as the chiral starting material and a combination of intramolecular alkyation and Criegee fragmentation have been employed for intramolecular stereospecific transfer of the chirality. An intramolecular diazoketone cyclopropanation and regioselective cyclopropane ring cleavage reactions have been employed for the creation of the three requisite contiguous quaternary carbon atoms.
An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes
Srikrishna,Anebouselvy
, p. 7102 - 7106 (2007/10/03)
An enantiospecific approach to mayurone and thujopsenes, sesquiterpenes containing three contiguous quaternary carbon atoms, starting from (R)-carvone (8), is described. (S)-3,4,4-Trimethylcarvone (7), obtained from (R)-carvone, was transformed into the bicyclo[2.2.2]octanone 13 via regioselective intramolecular alkylation of the allyl bromide 11. Regioselective ozonolysis and Criegee fragmentation of the bicyclic ketone 13 furnished the keto ester 14. Reductive deoxygenation followed by one-carbon homologation transformed the keto ester 19 into the ester 6. Intramolecular cyclopropanation of the diazo ketone 25, derived from the acid 5, furnished (-)dihydromayurone (4), thus constituting a formal enantiospecific synthesis of mayurone and thujopsenes.
