Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol

Herdeis, Claus; Mohareb, Rafat M.; Neder, Reinhard B.; Schwabenländer, F.; Telser, Joachim

doi:10.1016/s0957-4166(99)00466-8

Cited by 25 publications

(1 citation statement)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Paulsen found evidence for an intermediate equilibrium involving a bicyclic N,O-acetal and a cyclic imine. Similar results were found by Herdeis and co-workers 64 in their synthesis of the azepane core of the natural product Subsequently, Closa and co-workers observed that when the isoxazolidinium salt 28 was subjected to zinc-mediated reduction in aqueous hydrochloric acid followed by treatment with sodium methoxide (NaOMe) in refluxing methanol, the azabicycle 29 was isolated in 53% overall yield as a single isomer. The reaction proceeded via a cycloaddition-reduction-epimerization sequence, and also gave another product identified as tricycle 30 (4% yield).…”

Section: Systems With a 13-oxazepane Coresupporting

confidence: 81%

2,8-Diheterobicyclo[3.2.1]octane Ring Systems: Natural Occurrence, Synthesis and Properties

Flores

Dı́ez

2014

Synlett

View full text Add to dashboard Cite

This account describes the developments on the synthesis and reactivity of functionalized 2,8-diheterobicyclo[3.2.1]octanes. The continued interest in the chemistry of these compounds is mainly due to their abundance in Nature, being at the core of numerous families of biologically active natural products, and also as a result of their versatile reactivity, which makes them very useful building blocks with considerable impact in modern organic synthesis. The present article is aimed toward providing a comprehensive coverage of the literature on these heterocyclic scaffolds, including our own contributions, and has been organized according to the nature of the heteroatom embedded in the 2,8-bicyclo[3.2.1]octane framework.

show abstract

Section: Systems With a 13-oxazepane Coresupporting

confidence: 81%