Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone
A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman-Waiss lactone starting frommeso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5Sstere...
| Published in: | ACS Omega |
|---|---|
| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society
2021
|
| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85115987386&doi=10.1021%2facsomega.1c03251&partnerID=40&md5=ba02bcad1df9b17b1fd51e8216f8757f |
| id |
2-s2.0-85115987386 |
|---|---|
| spelling |
2-s2.0-85115987386 Ali M.T.M.; Husin Z.M.; Macabeo A.P.G. Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone 2021 ACS Omega 6 38 10.1021/acsomega.1c03251 https://www.scopus.com/inward/record.uri?eid=2-s2.0-85115987386&doi=10.1021%2facsomega.1c03251&partnerID=40&md5=ba02bcad1df9b17b1fd51e8216f8757f A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman-Waiss lactone starting frommeso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5Sstereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids. © 2021 The Authors. Published by American Chemical Society American Chemical Society 24701343 English Article All Open Access; Gold Open Access |
| author |
Ali M.T.M.; Husin Z.M.; Macabeo A.P.G. |
| spellingShingle |
Ali M.T.M.; Husin Z.M.; Macabeo A.P.G. Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| author_facet |
Ali M.T.M.; Husin Z.M.; Macabeo A.P.G. |
| author_sort |
Ali M.T.M.; Husin Z.M.; Macabeo A.P.G. |
| title |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| title_short |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| title_full |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| title_fullStr |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| title_full_unstemmed |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| title_sort |
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman-Waiss Lactone |
| publishDate |
2021 |
| container_title |
ACS Omega |
| container_volume |
6 |
| container_issue |
38 |
| doi_str_mv |
10.1021/acsomega.1c03251 |
| url |
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85115987386&doi=10.1021%2facsomega.1c03251&partnerID=40&md5=ba02bcad1df9b17b1fd51e8216f8757f |
| description |
A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman-Waiss lactone starting frommeso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5Sstereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids. © 2021 The Authors. Published by American Chemical Society |
| publisher |
American Chemical Society |
| issn |
24701343 |
| language |
English |
| format |
Article |
| accesstype |
All Open Access; Gold Open Access |
| record_format |
scopus |
| collection |
Scopus |
| _version_ |
1809678027461754880 |