Tremorgenic indole alkaloids. Studies directed toward the assembly of the A, F, and I rings of penitrem D: observation of an unexpected stereochemical outcome.
[formula: see text] In this Letter we demonstrate the viability of a highly stereoselective tandem Mannich cyclization-grammine fragmentation/addition cascade, critical for assembly of the A and F rings of penitrem D. We also explored simultaneous execution of this tactic with concurrent construction of ring I. Reinvestigation of a model system provided an explanation for the unanticipated stereochemical outcome at C(28).
Smith
A B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia 19104, USA. smithab@sas.upenn.edu
Kanoh
N
N
Minakawa
N
N
Rainier
J D
JD
Blase
F R
FR
Hartz
R A
RA
D000470:Alkaloids / Q000009:adverse effects / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry*; D013237:Stereoisomerism; D014202:Tremor / Q000139:chemically induced*
D000470:Alkaloids; D007211:Indoles; D009183:Mycotoxins; C003626:tremortin