Total solid phase syntheses of the quinazoline alkaloids: verrucines A and B and anacine.
The first total syntheses of verrucines A and B and anacine (revised structure) were accomplished on Sasrin resin. This work confirmed the structure of verrucine A and unambiguously showed verrucine B to be a derivative of D-phenylalanine and L-glutamine. The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. 1-Hydroxyverrucine B, derived from air oxidization of verrucine B, was also isolated and characterized.
Wang
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Institute of Molecular and Cell Biology, 30 Medical Drive, Singapore 117609, Singapore.
Sim
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MM
D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
C445699:1-hydroxyverrucine B; D000470:Alkaloids; D011799:Quinazolines; D012116:Resins, Plant; C445698:anacine alkaloid; C445696:verrucine A; C445697:verrucine B