Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene A synthesis Journal Article
| Authors: | Cheong, P. H. Y.; Yun, H.; Danishefsky, S. J.; Houk, K. N. |
| Article Title: | Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene A synthesis |
| Abstract: | The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions. © 2006 American Chemical Society. |
| Keywords: | chemistry; models, molecular; crystallography, x-ray; chemical structure; molecular structure; conformation; x ray crystallography; molecular conformation; synthesis; stereoisomerism; diterpene; diterpenes; guanacastepene |
| Journal Title: | Organic Letters |
| Volume: | 8 |
| Issue: | 8 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2006-04-13 |
| Start Page: | 1513 |
| End Page: | 1516 |
| Language: | English |
| DOI: | 10.1021/ol052862g |
| PUBMED: | 16597098 |
| PROVIDER: | scopus |
| PMCID: | PMC3164362 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 17" - "Export Date: 4 June 2012" - "Source: Scopus" |
