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Expedient Construction of the Hexacycle of Franchetine
Author(s) -
Lv Zhengchao,
Gao Lingzhi,
Cheng Chuanxu,
Niu Wei,
Wang JianLi,
Xu Liang
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800116
Subject(s) - stereocenter , stereochemistry , ring (chemistry) , chemistry , bridging (networking) , combinatorial chemistry , enantioselective synthesis , computer science , organic chemistry , catalysis , computer network
Franchetine, a unique 7,17‐ seco type of norditerpenoid alkaloid, possesses a highly congested polycyclic architecture coupled with nine stereogenic centers. Here we present an efficient synthetic approach for the intact hexacyclic framework of franchetine from the known tricyle 16 in 20 steps. The synthesis features a diastereoselective 6‐exo‐tet radical cyclization for construction of ring A and a unique oxidative Wagner–Meerwein‐type rearrangement to realize the functionalized [3.2.1] bridging ring CD.