Ring‐Closing Metathesis and Photo‐Fries Reaction for the Construction of the Ansamycin Antibiotic Kendomycin: Development of a Protecting Group Free Oxidative Endgame | Zendy

Magauer Thomas | Zendy; Martin Harry J. | Zendy; Mulzer Johann | Zendy

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Ring‐Closing Metathesis and Photo‐Fries Reaction for the Construction of the Ansamycin Antibiotic Kendomycin: Development of a Protecting Group Free Oxidative Endgame

Author(s) -

Magauer Thomas,

Martin Harry J.,

Mulzer Johann

Publication year - 2010

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.200902226

Subject(s) - polyketide , ring closing metathesis , total synthesis , metathesis , stereochemistry , chemistry , ring (chemistry) , protecting group , double bond , chess endgame , salt metathesis reaction , combinatorial chemistry , organic chemistry , computer science , biosynthesis , alkyl , artificial intelligence , polymerization , enzyme , polymer

Two convergent total syntheses of the ansa ‐polyketide (−)‐kendomycin ( 1 ) are described. The syntheses benefit from the use of readily available and cheap starting materials. Highly complex diastereoselective Claisen–Ireland rearrangements were used to introduce the ( E )‐double bond and the C16‐Me group. The ring closure of the strained ansa macrocycle was achieved by ring‐closing metathesis and a highly efficient combination of macrolactonization and photo‐Fries reaction. A protecting group free endgame via an unstable o ‐quinone is presented. Additionally some unsuccessful synthetic efforts towards the total synthesis of 1 are described.

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