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Studies on the Total Synthesis of Hirtellanine A: Regioselective Synthesis of Benzopyran
Author(s) -
Zheng Shuyan,
Li Xiaoping,
Tan Hongsheng,
Yu Chunhui,
Zhang Jinghua,
Shen Zhengwu
Publication year - 2013
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.201201339
Subject(s) - chemistry , regioselectivity , benzopyran , aryl , phloroglucinol , total synthesis , tautomer , cascade reaction , claisen rearrangement , tandem , iodide , bromide , combinatorial chemistry , derivative (finance) , organic chemistry , alkyl , materials science , financial economics , economics , composite material , catalysis
The total synthesis of Hirtellanine A was accomplished by two different synthetic approaches. Hirtellanine A was assembled using a one‐pot, tandem acid‐mediated deprotection and tautomerization cascade starting from quinone derivative 23 . The key features of the synthesis include a Houben–Hoesch reaction of aryl cyanide 3 with phloroglucinol, a one‐pot sequential boronation, a Suzuki–Miyaura cross‐coupling of aryl bromide 33 with aryl iodide 26 , and a base‐mediated regioselective Claisen rearrangement for the benzopyran construction.