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,...

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Bibliographic Details
Published in:Organic letters 2003-03, Vol.5 (5), p.765-768
Main Authors: Neubert, Bobbianna J, Snider, Barry B
Format: Article
Language:English
Subjects:
Alkylation
Animals
Antibiotics, Antineoplastic - chemical synthesis
Cyclization
Indicators and Reagents
Porifera - chemistry
Pyridinium Compounds - chemical synthesis
Pyrroles - chemical synthesis
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034042e