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Synthesis of (+/-)-phloeodictine A1
Journal article   Peer reviewed

Synthesis of (+/-)-phloeodictine A1

Bobbianna J Neubert and Barry B Snider
Organic Letters, Vol.5(5), pp.765-768
03/01/2003
PMID: 12605510

Abstract

Animals Pyrroles - chemical synthesis Cyclization Stereoisomerism Antibiotics, Antineoplastic - chemical synthesis Indicators and Reagents Porifera - chemistry Pyridinium Compounds - chemical synthesis Alkylation
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.

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