Unknown

Dataset Information

0

Synthesis of 2,6-trans-disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols.

ABSTRACT: Certain (Z)-1,5-syn-diols 2 may be converted into 2,6-trans-5,6-dihydropyrans by using phosphonium salt 4 or phosphorane 5 as dehydrating agents. A more general four step procedure converts the (Z)-1,5-syn-endiols into enantiomeric dihydropyrans ent-3 via regioselective silylation of the allylic alcohol unit followed by mesylate formation and base-promoted nucleophilic displacement.

SUBMITTER: Flamme EM 

PROVIDER: S-EPMC1399455 | biostudies-literature | 2005 Aug

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Synthesis of 2,6-trans-disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols.

Flamme Eric M EM   Roush William R WR  

Beilstein journal of organic chemistry 20050826 1

Certain (Z)-1,5-syn-diols 2 may be converted into 2,6-trans-5,6-dihydropyrans by using phosphonium salt 4 or phosphorane 5 as dehydrating agents. A more general four step procedure converts the (Z)-1,5-syn-endiols into enantiomeric dihydropyrans ent-3 via regioselective silylation of the allylic alcohol unit followed by mesylate formation and base-promoted nucleophilic displacement. ...[more]

Similar Datasets

Unknown Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.
| S-EPMC2777747 | biostudies-literature
Unknown Synthesis of symmetrical 1,5-disubstituted granatanines.
| S-EPMC3652803 | biostudies-literature
Unknown Synthesis of 2,6-disubstituted tetrahydroazulene derivatives.
| S-EPMC3388855 | biostudies-literature
Unknown Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.
| S-EPMC2597462 | biostudies-literature
Unknown Synthesis and antimalarial activity of 3,3-spiroanellated 5,6-disubstituted 1,2,4-trioxanes.
| S-EPMC4027577 | biostudies-literature
Unknown Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.
| S-EPMC2755244 | biostudies-literature
Unknown Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.
| S-EPMC1480410 | biostudies-literature
Unknown A bidirectional S(E)' strategy for 1,5-syn and 1,5-anti stereocontrol toward the synthesis of complex polyols.
| S-EPMC3565749 | biostudies-literature
Unknown Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles.
| S-EPMC5727845 | biostudies-literature
Unknown Synthesis of <i>Cis</i>,<i>syndiotactic</i> A<i>-alt</i>-B Copolymers from Two Enantiomerically Pure <i>Trans</i>-2,3-Disubstituted-5,6-Norbornenes.
| S-EPMC5043441 | biostudies-literature