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Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.

ABSTRACT: The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8- endo-dig hydroarylation and a 6- exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.

SUBMITTER: Miloserdov FM

PROVIDER: S-EPMC5920919 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.

Miloserdov Fedor M FM Kirillova Mariia S MS Muratore Michael E ME Echavarren Antonio M AM

Journal of the American Chemical Society 20180222 16

The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8- endo-dig hydroarylation and a 6- exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided. ...[more]

PMID: 29432680

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