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Biomimetic Explorations Towards the Bisorbicillinoids: Total Synthesis of Bisorbicillinol, Bisorbibutenolide, and Trichodimerol
Author(s) -
Nicolaou K. C.,
Simonsen Klaus B.,
Vassilikogiannakis Georgios,
Baran Phil S.,
Vidali Veroniki P.,
Pitsinos Emmanuel N.,
Couladouros Elias A.
Publication year - 1999
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/(sici)1521-3773(19991203)38:23<3555::aid-anie3555>3.0.co;2-z
Subject(s) - biomimetic synthesis , biomimetic materials , total synthesis , cascade , nanotechnology , chemistry , combinatorial chemistry , stereochemistry , materials science , chromatography
Strikingly simple cascade dimerization sequences can be used to assemble the complex frameworks of bisorbicillinoids such as bisorbicillinol ( 1 ), bisorbibutenolide ( 2 ), and trichodimerol ( 3 ). The mechanistic facets of the biomimetic total syntheses of these bioactive natural products were also explored. Inspection of the unique molecular architecture of these compounds reveals that they are likely to be assembled in nature by a dimerization of two oxidized forms of sorbicillin.