Efficient construction of the securine A carbon skeleton | Zendy

Peter Korakas | Zendy; Stuart C. Chaffee | Zendy; J. Brad Shotwell | Zendy; Pamela Duque | Zendy; John L. Wood | Zendy

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Efficient construction of the securine A carbon skeleton

Author(s) -

Peter Korakas,

Stuart C. Chaffee,

J. Brad Shotwell,

Pamela Duque,

John L. Wood

Publication year - 2004

Publication title -

proceedings of the national academy of sciences

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.011

H-Index - 771

eISSN - 1091-6490

pISSN - 0027-8424

DOI - 10.1073/pnas.0402274101

Subject(s) - ring (chemistry) , chemistry , stereochemistry , azide , carbon skeleton , tandem , combinatorial chemistry , organic chemistry , materials science , composite material

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.

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