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Biomimetic Cationic Cyclization toward ent ‐Kaurene‐type Diterpenoids
Author(s) -
Zhu Lili,
Hong Ran
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201201029
Subject(s) - chemistry , diterpene , polyene , stereochemistry , carbocation , biomimetic synthesis , terpenoid , cationic polymerization , biosynthesis , cyclase , acetal , organic chemistry , enzyme
Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from ( E , E , E )‐geranylgeranyl diphosphate (GGPP). From GGPP, diterpene cyclase catalyzes a sequence of carbocation‐mediated cyclizations, rearrangements, and further oxidations, leading to a class of structurally unique ent ‐kaurenes, such as cafestol, gibberellin A3 and oridonin. According to the biosynthesis pathway of ent ‐kaurene, we designed a chiral acetal‐enabled and SnCl 4 ‐promoted biomimetic polyene cationic cyclization. With a following Birch reduction/alkylation cascade, a core skeleton of representative ent ‐kaurenes diterpenoids was completed.