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- Title
Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids.
- Authors
Liu, Yun ‐ Ting; Li, Lin ‐ Ping; Xie, Jian ‐ Hua; Zhou, Qi ‐ Lin
- Abstract
A concise, divergent, asymmetric total syntheses of mulinane diterpenoids has been achieved. Specifically, a new strategy was developed featuring a key intramolecular Friedel-Crafts reaction to construct the chiral fused 5-6-6 tricyclic motif, followed by sequential Birch reduction, conjugate methylation, and homologation/ring-expansion reactions to furnish the desired 5-6-7 tricyclic skeleton bearing five contiguous stereocenters. With this efficient strategy, seven mulinane diterpenoids and two analogues were synthesized via late-stage functional modification or functionalization in 8.6-20 % overall yields and 11-15 steps.
- Subjects
DITERPENES; INTERMOLECULAR interactions; FRIEDEL-Crafts reaction; BIRCH reduction; FUNCTIONAL groups
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 41, p12882
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201706994