New total synthesis of the marine antitumor alkaloid (-)-agelastatin A.
[reaction: see text] A new total synthesis of (-)-agelastatin A (1) has been achieved from the chiral oxazolidinone (-)-3. Although enone transposition was problematic when the Michael ring closure of 2 was attempted with strong base, the desired cyclization could be effected with Hunig's base after the pyrrole nucleus was brominated. Subsequent reduction and monobromination afforded synthetic (-)-agelastatin A (1).
Domostoj
Mathias M
MM
The Christopher Ingold Laboratories, The Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, United Kingdom.
Irving
Ed
E
Scheinmann
Feodor
F
Hale
Karl J
KJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D023303:Oxazolidinones; C464968:agelastatin A