In:
Organic & Biomolecular Chemistry, Royal Society of Chemistry (RSC), Vol. 19, No. 42 ( 2021), p. 9190-9198
Abstract:
Chiral heteropolycyclic structures are widespread in compounds of high pharmaceutical relevance. In particular, linear fused pyran-dioxane based polycycles can be found in several naturally occurring molecules, and among them, cardiac glycosides and antibiotic spectinomycin are characterized by a cis – cisoid – trans geometry. Then, the stereocontrol in the synthesis of this type of polycyclic scaffold is of primary importance. Herein, we present two novel linear fused pyran-dioxane based bi- and tricycles, synthesized with total stereoselectivity from a glycal derived vinyl epoxide. The straightforward methodology described involves a substrate-dependent stereospecific glycosylation step followed by an intramolecular S N 2′ conjugate addition process, leading to a pyran-dioxane-cyclohexane tricycle with a cis – cisoid – trans stereochemistry, in agreement with the geometry of many natural products. The stereochemical analysis of these compounds, which was realized by a combined NMR/computational approach, is also reported.
Type of Medium:
Online Resource
ISSN:
1477-0520
,
1477-0539
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2021
detail.hit.zdb_id:
2097583-1
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