Stereochemical course of direct ring closures of complex homoallylic alcohols to substituted tetrahydrofurans

Mihelich, Edward D.; Hite, G. A.

doi:10.1021/ja00044a066

Cited by 59 publications

(18 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Interestingly, the two hydrogens H-1b (δ H 3.94) and H-4b (δ H 3.70) were up-field shifted compared to hydrogens H-1a (δ H 4.10) and H-4a (δ H 4.00) supporting that H-1b and H-4b are synfacial to the two oxygenated groups, 2-O-benzoyl and 3-OH, respectively. Effects of substituents on 1 H chemical shifts of non-equivalent methylene protons in some tetrahydrofuran derivatives were reported (Mihelich and Hite, 1992;Brovetto and Seoane, 2008;Yoshimatsu et al, 1996;Williams et al, 1984) (see Fig. S3).…”

Section: Resultsmentioning

confidence: 99%

New erythritol derivatives from the fertile form of Roccella montagnei

Duong¹,

Huynh²,

Chavasiri

et al. 2017

Phytochemistry

View full text Add to dashboard Cite

Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC value of 68.39 ± 3.46 μM.

show abstract

Section: Resultsmentioning

confidence: 99%

New erythritol derivatives from the fertile form of Roccella montagnei

Duong¹,

Huynh²,

Chavasiri

et al. 2017

Phytochemistry

View full text Add to dashboard Cite

show abstract

“…With more complex substrates, the dehydration/cyclisation step was accompanied by loss of phenylselenenic acid giving the returned alkenol as the major product. 6 It transpired that direct cyclisation using either phenylselenenyl chloride 7 or phthalimide 8 in the presence of 20 mol% of tin(IV) chloride was more successful and led to the completion of syntheses of the methyl ester of nonactic acid 2 and pamamycin 607 1. 9 During the course of this work it was necessary to prepare a sample of a cis-2,5-disubstituted tetrahydrofuran by a stereochemically unambiguous route.…”

Section: Introductionmentioning

confidence: 99%

Stereocontrolled syntheses of 2,5-disubstituted tetrahydrofurans using remote asymmetric induction

Hobson¹,

Singh²,

Thomas³

2001

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Depending on the alkene and on the selenium electrophile, cyclizations can be performed with high selectivities. The size of the electrophilic reagent has a large influence on the diastereomeric ratio of the 39 and 40, which varies from 4:1 [46] to > 49:1 (Scheme 13). [47] OH Me Me C 6 …”

mentioning

confidence: 99%

Organoselenium Chemistry in Stereoselective Reactions

Wirth

2000

Angew. Chem. Int. Ed.

302

188

View full text Add to dashboard Cite

Selenium‐based methods have developed rapidly over the past few years asnd organoselenium chemistry has become a very useful tool in the hands of synthetic chemists. The different reactivity of selenium‐containing compounds in contrast to the sulfur analogues has led to versatile and new synthetic methods in organic chemistry. Various functionalities can be selectively introduced into complex molecules under very mild reaction conditions. In this review, the principles of organoselenium chemistry are traced back to their origins and are highlighted with respect to stereoselective synthesis. The unique properties of selenium allow the development of new and highly selective transformations, which can be employed subsequently in new routes for the synthesis of versatile chiral building blocks and for natural product synthesis.

show abstract

Stereochemical course of direct ring closures of complex homoallylic alcohols to substituted tetrahydrofurans

Cited by 59 publications

References 1 publication

New erythritol derivatives from the fertile form of Roccella montagnei

New erythritol derivatives from the fertile form of Roccella montagnei

Stereocontrolled syntheses of 2,5-disubstituted tetrahydrofurans using remote asymmetric induction

Organoselenium Chemistry in Stereoselective Reactions

Contact Info

Product

Resources

About