β-Lactones are a class of structurally unique compounds. The versatile reactivity patterns offered by β-lactones have enable chemists to utilize them as powerful synthetic vehicles in complex molecule synthesis.
In the total syntheses of the naturally occurring, α-glucosidase inhibitors schulzeines B & C, a readily available trichloromethyl β-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 β-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, β-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.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/ETD-TAMU-2011-12-10494 |
| Date | 2011 December 1900 |
| Creators | Liu, Gang |
| Contributors | Romo, Daniel, Connell, Brian T., Yang, Jiong, Qin, Hongmin |
| Source Sets | Texas A and M University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis, thesis, text |
| Format | application/pdf |
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