Reconciling icetexane biosynthetic connections with their chemical synthesis: total synthesis of (+/-)-5,6-dihydro-6alpha-hydroxysalviasperanol, (+/-)-brussonol, and (+/-)-abrotanone.
A unified strategy for the chemical synthesis of the icetexane diterpenoids brussonol and 5,6-dihydro-6alpha-hydroxysalviasperanol has led to a structural revision of the recently isolated natural products abrotandiol and abrotanone.
Simmons
Eric M
EM
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Yen
Jennifer R
JR
Sarpong
Richmond
R
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018547:Plant Stems / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D027544:Salvia / Q000737:chemistry
C522056:5,6-dihydro-6alpha-hydroxysalviasperanol; D004224:Diterpenes; D007202:Indicators and Reagents; C522057:abrotanone; C502780:brussonol