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Efficient construction of the securine A carbon skeleton.

ABSTRACT: Securamine A is a structurally intriguing alkaloid possessing a pyrroloindole core joined via a modified isoprene subunit to a functionalized imidazole ring. Recent synthetic efforts in this laboratory have resulted in the efficient construction of key lactone 36, which undergoes tandem azide reduction/ring expansion to macrolactam 37. Macrolactam 37 possesses the complete macrocyclic core of securamine A.

SUBMITTER: Korakas P

PROVIDER: S-EPMC514433 | biostudies-other | 2004 Aug

REPOSITORIES: biostudies-other

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Efficient construction of the securine A carbon skeleton.

Korakas Peter P Chaffee Stuart S Shotwell J Brad JB Duque Pamela P Wood John L JL

Proceedings of the National Academy of Sciences of the United States of America 20040727 33

Securamine A is a structurally intriguing alkaloid possessing a pyrroloindole core joined via a modified isoprene subunit to a functionalized imidazole ring. Recent synthetic efforts in this laboratory have resulted in the efficient construction of key lactone 36, which undergoes tandem azide reduction/ring expansion to macrolactam 37. Macrolactam 37 possesses the complete macrocyclic core of securamine A. ...[more]

PMID: 15280544

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