Total syntheses of schulzeines B and C.
Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihydroxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.
Gurjar
Mukund K
MK
National Chemical Laboratory, Dr. Homi Bhabha Road, Pune - 411 008, India. mk.gurjar@ncl.res.in
Pramanik
Chinmoy
C
Bhattasali
Debabrata
D
Ramana
C V
CV
Mohapatra
Debendra K
DK
D001688:Biological Products / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D001688:Biological Products; D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; C523671:schulzeine B; C523672:schulzeine C