Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 16, Pages 6114-6117Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1115524
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Funding
- National Science Foundation [0135031, 0806356]
- University of California Tobacco
- ACS Division of Organic Chemistry (SURF)
- Pfizer-La Jolla
- UCSB
- Direct For Mathematical & Physical Scien [0806356, 0135031] Funding Source: National Science Foundation
- Division Of Chemistry [0806356, 0135031] Funding Source: National Science Foundation
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An expeditious convergent total synthesis affords (+/-)-gamma-rubromycin (1) in 4.4% overall yield. The longest linear sequence is 12 steps from commercial starting materials. The effort highlights a remarkable late-stage oxidative [3 + 2] cycloaddition for construction of the spiroketal, a regioselective carbonyl methylenation, a boron tribromide promoted deprotection, ortho- to para-naphthoquinone spiroketal rearrangement, and a tautomerization sequence.
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