Total Synthesis of Salimabromide: A Tetracyclic Polyketide from a Marine Myxobacterium | Zendy

Matthias Schmid | Zendy; Adriana S. Grossmann | Zendy; Klaus Wurst | Zendy; Thomas Magauer | Zendy

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Total Synthesis of Salimabromide: A Tetracyclic Polyketide from a Marine Myxobacterium

Author(s) -

Matthias Schmid,

Adriana S. Grossmann,

Klaus Wurst,

Thomas Magauer

Publication year - 2018

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.8b06228

Subject(s) - polyketide , stereocenter , chemistry , stereochemistry , obligate , total synthesis , cycloaddition , combinatorial chemistry , enantioselective synthesis , organic chemistry , biosynthesis , botany , catalysis , biology , enzyme

Salimabromide is an antibiotic polyketide that was previously isolated from the obligate marine myxobacterium Enhygromyxa salina, and its densely functionalized and conformationally rigid tetracyclic framework is unprecedented in nature. Herein we report the first chemical synthesis of the target structure by employing a series of well-orchestrated, robust transformations, highlighted by an acid-promoted, powerful Wagner-Meerwein rearrangement/Friedel-Crafts cyclization sequence to forge the two adjacent quaternary carbon centers embedded in the tetrahydronaphthalene. A high-yielding ketiminium mediated [2+2]-cycloaddition was also utilized for the simultaneous construction of the remaining three stereocenters.

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