Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 42, Pages 17714-17721Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3076988
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Funding
- NSF [CHE-0844593]
- Columbia University
- ACS Petroleum Research Fund [47481-G]
- Camille and Henry Dreyfus Foundation
- Eli Lilly
- Bristol-Myers Squibb
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [844593] Funding Source: National Science Foundation
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Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family of natural products, leading to the shortest syntheses of any member to date. These efforts include racemic formal total syntheses of laurefucin and E- and Z-pinnatifidenyne as well as a facile preparation of the oxocene core of 3E-dehydrobromolaurefucin. The key elements of the design are novel diastereoselective ring-expanding bromoetherifications of tetrahydrofurans triggered by a unique bromonium source (BDSB, Et2SBr center dot SbBrCl5) and strategically positioned nucleophilic traps, where altering the identity and position of these traps affords diverse functionality on the eight-membered ring backbone. Its biogenetic relevance is also discussed in light of the range of substrates that successfully undergo this key rearrangement.
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