Open AccessEfficient 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 of the united states of america
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.