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Synthesis of 12,12′-azo-13,13′-diepi-Ritterazine N.
- Source :
-
Journal of Organic Chemistry . 1/6/2017, Vol. 82 Issue 1, p269-275. 7p. - Publication Year :
- 2017
-
Abstract
- 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 β-OH ketone from the isoxazoline ring, we end up with a synthesis of a cyclic analogue of ritterazine N. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 82
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 120716260
- Full Text :
- https://doi.org/10.1021/acs.joc.6b02391