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Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids
Author(s) -
Liu YunTing,
Li LinPing,
Xie JianHua,
Zhou QiLin
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706994
Subject(s) - stereocenter , intramolecular force , total synthesis , chemistry , conjugate , stereochemistry , friedel–crafts reaction , structural motif , ring (chemistry) , divergent synthesis , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis , biochemistry
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.