Traceless Solid-Phase Synthesis of Fused Chiral Macrocycles via Conformational Constraint-Assisted Cyclic Iminium Formation

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583791" target="_blank" >RIV/61989592:15110/17:73583791 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/17:73583791

Result on the web

<a href="http://onlinelibrary.wiley.com/doi/10.1002/chem.201702461/epdf" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/chem.201702461/epdf</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.201702461" target="_blank" >10.1002/chem.201702461</a>

Result language

angličtina

Original language name

Traceless Solid-Phase Synthesis of Fused Chiral Macrocycles via Conformational Constraint-Assisted Cyclic Iminium Formation

Original language description

Natural products comprising chiral molecular scaffolds containing fused medium-sized cycles and macrocycles represent an important and relevant pharmacological target for the discovery and development of new drugs. Here, we describe traceless solid-phase synthesis of acyclic intermediates amenable to cyclization to medium (11) and large (12) fused rings. The key aspect of the synthetic strategy is incorporation of a specific conformation constraint that facilitates cyclization in favor of 11- and 12-membered rings rather than possible 7-membered ones. The role of constraints in preorganization required for cyclization is supported by computational analysis. The synthesis involves cyclic N-sulfonyliminium-nucleophilic addition chemistry as the key ring-forming reaction and proceeds with complete stereocontrol of the newly formed stereogenic center. We document the scope and limitations of this strategy in the synthesis of 11+5, 11+6, 11+7, and 12+6 fused rings representing molecular scaffolds with 3D architecture that mimic complex natural products.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Chemistry: A European Journal

ISSN

0947-6539

e-ISSN

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Volume of the periodical

21

Issue of the periodical within the volume

37

Country of publishing house

DE - GERMANY

Number of pages

10

Pages from-to

12876-12885

UT code for WoS article

000411033800028

EID of the result in the Scopus database

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