Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 24, Pages 8829-8836Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5043462
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Funding
- National Science Foundation [CHE-1055441]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1055441] Funding Source: National Science Foundation
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Studies describe the total synthesis of (+)-ileabethoxazole (1) using a Stille cross-coupling reaction of propargylic stannanes with 5-iodo-1,3-oxazoles to produce 1,1-disubstituted allenes (11). An iron-mediated [2 + 2 + 1] carbocyclization yields a novel cyclopentenone for elaboration to 1. Site-selective palladium insertion reactions allow for regiocontrolled substitutions of the heterocycle. Asymmetric copper hydride reductions are examined, and strategies for the formation of the central aromatic ring are discussed.
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