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Total Synthesis of Ileabethoxazole, Pseudopteroxazole, and seco ‐Pseudopteroxazole
Author(s) -
Yang Ming,
Yang Xiaowen,
Sun Hongbin,
Li Ang
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201510568
Subject(s) - aromatization , alkyne , stereochemistry , stille reaction , chemistry , total synthesis , cascade , organic chemistry , catalysis , chromatography , polymer
The total syntheses of ileabethoxazole, pseudopteroxazole, and seco ‐pseudopteroxazole, three antituberculosis diterpenoids that had been isolated from Pseudopterogorgia elisabethae , were accomplished in a collective fashion. A cascade alkyne carbopalladation/Stille reaction was exploited to construct a triene precursor with suitable geometry. A fully substituted arene was then assembled through a key 6π electrocyclization/aromatization sequence, and served as an advanced common intermediate. Two radical cyclizations led to the formation of the five‐ and six‐membered rings of ileabethoxazole and pseudopteroxazole, respectively, with the desired stereochemistry, and a straightforward side‐chain elongation delivered seco ‐pseudopteroxazole.