Roseophilin synthesis skeletal reorganization

Trost succeeded in formal total synthesis of roseophilin. Macrocyclic compound 118 is synthesized from enyne 117 by platinum-catalyzed skeletal reorganization reaction and is converted into 119, which is further converted into pyrrole derivative 120 (Scheme 43). ... 

Trost and Doherty applied the Pt-catalyzed skeletal reorganization reaction of enyne 281 to the construction of bicyclic compound 282 for the formal total synthesis of roseophilin 285, which was isolated from Streptomyces... 

SCHEME 24,69. Pt-catalyzed skeletal reorganization for the synthesis of roseophilin. 

Trost et al. succeeded in the formal total synthesis of roseophilin [34]. Macrocyclic compound 121 was synthesized from ene-yne 120 by platinum-catalyzed skeletal reorganization. From 121, the 1,4-diketone 122 was synthesized and converted to pyrrole derivative whose transformation into roseophilin had previously been reported (Scheme 6.28). 

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