期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 10, 页码 3898-3908出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200332d
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资金
- University of Alabama
- National Science Foundation [CHE-0845011]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0845011] Funding Source: National Science Foundation
The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the desired compound that does not spectroscopically correlate to the initially described natural product.
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