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Enantioselective Total Synthesis of Blennolide H and Phomopsis‐H76 A and Determination of Their Structure
Author(s) -
Valdomir Guillermo,
Senthilkumar Soundararasu,
Ganapathy Dhandapany,
Zhang Yun,
Tietze Lutz F.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801323
Subject(s) - enantioselective synthesis , phomopsis , chemistry , stereochemistry , botany , biology , organic chemistry , catalysis
This work reports on the enantioselective total synthesis of the two dimeric natural chromanone lactones phomopsis‐H76 A ( 5 ) and blennolide H ( 6 ). Both syntheses could be achieved from chromane 11, which was obtained by an enantioselective Wacker‐type cyclization with >99 % ee . The dimerization of the corresponding monomers was performed using a palladium‐catalyzed Suzuki reaction. Moreover, within this work it was possible to revise the absolute configuration of phomopsis‐H76 A and determine the relative as well as absolute configuration of blennolide H.