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 |
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| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society
2021
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85115987386&doi=10.1021%2facsomega.1c03251&partnerID=40&md5=ba02bcad1df9b17b1fd51e8216f8757f |
| Summary: | 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 |
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| ISSN: | 24701343 |
| DOI: | 10.1021/acsomega.1c03251 |