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Total Synthesis of (±)‐8‐Oxo‐erythrinine, (±)‐8‐Oxo‐erythraline, and (±)‐Clivonine
Author(s) -
He Maomao,
Qu Chunrong,
Ding Bingbing,
Chen Hao,
Li Yangyan,
Qiu Guofu,
Hu Xianming,
Hong Xuechuan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500265
Subject(s) - chemistry , intramolecular force , total synthesis , stereochemistry , lycorine , ring (chemistry) , radical cyclization , stereocenter , erythrina , block (permutation group theory) , combinatorial chemistry , alkaloid , enantioselective synthesis , organic chemistry , combinatorics , traditional medicine , medicine , mathematics , catalysis
Total syntheses of the erythrina alkaloids (±)‐8‐oxo‐erythrinine and (±)‐8‐oxo‐erythraline have been developed, based on a substrate‐controlled intramolecular 6‐ exo ‐ trig selective radical spirocyclization that establishes the quaternary center of the B‐rings. An improved total synthesis of (±)‐clivonine has also been reported, based on an intramolecular 6‐ endo‐trig free‐radical cyclization of a highly functionalized enamide, and a biomimetic ring‐switch of a lycorine‐type intermediate. These endo / exo ‐selective sequences enabled us to rapidly assemble two different complex alkaloids from a common building block in an economical fashion.