期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 1, 页码 269-275出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02391
关键词
-
资金
- National Natural Science Foundation of China [21272258, 21572248]
A synthesis of the 12,12'-azo-analogue of ritterazine N from hecogenin is reported. Ring: contraction of two 6/5 bicyclic ring systems, one trans-fused and another spiro, to 5/5 spiro ring systems is accomplished with excellent stereochemical control. Key transformations include an abnormal Baeyer-Villiger oxidation, a Norrish type I cleavage, an intramolecular dipolar [3 + 2] cycloaddition, and an intramolecular oxymecuration. Failing to uncover the beta-OH ketone from the isoxazoline ring, we end up with a synthesis of a cyclic analogue of ritterazine N.
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