Synthesis of (+/-)-phloeodictine A1.
The antitumor antibiotic phloeodictine A1 (2) has been synthesized by a convergent seven-step route in 8% overall yield. The key step was the Eguchi aza-Wittig reaction of 6 to give 13 followed by a retro Diels-Alder reaction to liberate 5. Addition of 11-dodecenylmagnesium bromide to 5 to give 4b, alkylation with 18b, and deprotection completed the first synthesis of 2.
Neubert
Bobbianna J
BJ
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Snider
Barry B
BB
D000478:Alkylation; D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D011161:Porifera / Q000737:chemistry; D011726:Pyridinium Compounds / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; D011726:Pyridinium Compounds; D011758:Pyrroles; C474591:phloeodictine A1