Efficient construction of the securine A carbon skeleton.
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.
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, CT 06514, USA.
Peter
P
Korakas
Stuart
S
Chaffee
J Brad
JB
Shotwell
Pamela
P
Duque
John L
JL
Wood
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002013:Bryozoa / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
D001688:Biological Products; D026121:Indole Alkaloids