Efficient construction of the securine A carbon skeleton.

Korakas, Peter; Chaffee, Stuart; Shotwell, J Brad; Duque, Pamela; Wood, John L · Proc Natl Acad Sci U S A · 2004

basic_science · Level V

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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.

Medical subject headings