Beta-Lactones as Synthetic Vehicles in Natural Product Synthesis: Total Syntheses of Schulzeines B & C and Omphadiol, and Studies toward the Total Syntheses of Scabrolides A & B and Sinulochmodin C
| dc.contributor | Romo, Daniel | |
| dc.creator | Liu, Gang | |
| dc.date.accessioned | 2014-01-15T07:05:30Z | |
| dc.date.accessioned | 2017-04-07T19:59:23Z | |
| dc.date.available | 2014-01-15T07:05:30Z | |
| dc.date.available | 2017-04-07T19:59:23Z | |
| dc.date.created | 2011-12 | |
| dc.date.issued | 2012-02-14 | |
| dc.description.abstract | ?-Lactones are a class of structurally unique compounds. The versatile reactivity patterns offered by ?-lactones have enable chemists to utilize them as powerful synthetic vehicles in complex molecule synthesis. In the total syntheses of the naturally occurring, ?-glucosidase inhibitors schulzeines B & C, a readily available trichloromethyl ?-lactone was used as a versatile masked surrogate for bishomoserine aldehyde, which led to a highly efficient construction of the core structures through a pivotal Pictet-Spengler condensation and a Corey-Link reaction. The first total synthesis of (+)-omphadiol was achieved in ten steps from (R)-carvone. This synthesis features a three-step synthesis of a bicyclic ?-lactone, which constitutes the key intermediate for the highly stereocontrolled introduction of the six contiguous stereogenic centers in the natural product. In efforts toward the total syntheses of scabrolides A & B and sinulochmodin C via transannular C-H insertions, ?-lactones served as the key intermediates for the synthesis of complex macrocyclic model substrates. These model studies provided valuable insights into the reactivity and selectivity issues for transannular C-H insertion reactions. | |
| dc.identifier.uri | http://hdl.handle.net/1969.1/ETD-TAMU-2011-12-10494 | |
| dc.language.iso | en_US | |
| dc.subject | ?-Lactones | |
| dc.subject | total synthesis | |
| dc.subject | schulzeines | |
| dc.subject | omphadiol | |
| dc.subject | scabrolides | |
| dc.subject | sinulochmodin C | |
| dc.title | Beta-Lactones as Synthetic Vehicles in Natural Product Synthesis: Total Syntheses of Schulzeines B & C and Omphadiol, and Studies toward the Total Syntheses of Scabrolides A & B and Sinulochmodin C | |
| dc.type | Thesis |