Journal
ORGANIC LETTERS
Volume 22, Issue 14, Pages 5550-5554Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01913
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Funding
- Royal Society of New Zealand Te Aparangi
- Kate Edger Educational Charitable Trust
- University of Auckland
- Maurice Wilkins Centre for Molecular Biodiscovery
- New Zealand Ministry of Business, Innovation and Employment [5000449]
- National Institute of General Medical Sciences [GM119426]
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The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex beta-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (-)-anthracimycin.
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