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Total Synthesis of Liangshanone
Author(s) -
Huang HongXiu,
Mi Fen,
Li Chunxin,
He Huan,
Wang FengPeng,
Liu XiaoYu,
Qin Yong
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011923
Subject(s) - chemistry , annulation , enantioselective synthesis , total synthesis , cycloaddition , stereochemistry , intramolecular force , alkene , aldol reaction , natural product , combinatorial chemistry , organic chemistry , catalysis
The first total synthesis of liangshanone, a hexacyclic ent ‐kaurane diterpenoid alkaloid, has been completed. Its intricate cagelike framework was assembled through several key transformations, including an oxidative dearomatization/Diels–Alder (OD/DA) cycloaddition sequence, a tandem alkene cleavage/Mannich cyclization, a Robinson‐type annulation, and an intramolecular aldol reaction. Notably, an organocatalytic enantioselective α‐hydroxymethylation process allowed the preparation of an enantiomerically enriched tricyclic intermediate that should enable asymmetric access to the target natural product.