Toward an integrated route to the vernonia allenes and related sesquiterpenoids
The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragme...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2011-07-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.7.104 |
| id |
doaj-025d205d228d4ee6b0a205ae7ee4b52f |
|---|---|
| record_format |
Article |
| spelling |
doaj-025d205d228d4ee6b0a205ae7ee4b52f2021-02-02T08:46:31ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-07-017193794310.3762/bjoc.7.1041860-5397-7-104Toward an integrated route to the vernonia allenes and related sesquiterpenoidsDa Xu0Michael A. Drahl1Lawrence J. Williams2Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854, USADepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854, USADepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854, USAThe synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed.https://doi.org/10.3762/bjoc.7.104C–C fragmentationendocyclic allenenatural producttotal synthesis |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Da Xu Michael A. Drahl Lawrence J. Williams |
| spellingShingle |
Da Xu Michael A. Drahl Lawrence J. Williams Toward an integrated route to the vernonia allenes and related sesquiterpenoids Beilstein Journal of Organic Chemistry C–C fragmentation endocyclic allene natural product total synthesis |
| author_facet |
Da Xu Michael A. Drahl Lawrence J. Williams |
| author_sort |
Da Xu |
| title |
Toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| title_short |
Toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| title_full |
Toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| title_fullStr |
Toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| title_full_unstemmed |
Toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| title_sort |
toward an integrated route to the vernonia allenes and related sesquiterpenoids |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2011-07-01 |
| description |
The synthesis of a model endocyclic allene related to the vernonia allenes is described. Fragmentation of a suitable decalin derivative gave the simplified germacrane scaffold. Computational analysis of this and related substrates provides insight into the stereoelectronic requirements of C–C fragmentation. The overall strategy to access these and other sesquiterpenes and the key steps in the present sequence are also discussed. |
| topic |
C–C fragmentation endocyclic allene natural product total synthesis |
| url |
https://doi.org/10.3762/bjoc.7.104 |
| work_keys_str_mv |
AT daxu towardanintegratedroutetothevernoniaallenesandrelatedsesquiterpenoids AT michaeladrahl towardanintegratedroutetothevernoniaallenesandrelatedsesquiterpenoids AT lawrencejwilliams towardanintegratedroutetothevernoniaallenesandrelatedsesquiterpenoids |
| _version_ |
1724296412985819136 |