Stereoselective synthesis of the C21–C29 fragment of (+)-Sorangicin A employing iodocyclization reactions

Mohapatra, Debendra K.; Banoth, Shivalal; Yadav, J. S.

doi:10.1016/j.tetlet.2015.09.037

Cited by 7 publications

(2 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From the retro‐synthetic analysis of 4 (Scheme ), the formation of the 14‐ lactone moiety was envisaged through Yamaguchi macrolactonization on the seco acid 5 , inturn seco acid envisaged by the cross metathesis of fragments 6 , known alcohol 7 . 2,6 dihydro‐2H‐pyran 6 was envisaged from hydroxy ester 8 , which in turn synthesized from known α, β‐unsaturated‐γ, δ‐epoxy ester 9 . The main objectives thus would be: a) stereoselective epoxide opening with benzyl alcohol with retention of stereo chemistry, b) I 2 mediated formation trans‐2,6‐disubstituted tetrahydro‐ 2H ‐pyran.…”

Section: Resultsmentioning

confidence: 99%

Studies towards the Total Synthesis of Aspergillide‐B

et al. 2018

View full text Add to dashboard Cite

A formal, stereoselective synthesis of Aspergillide‐B is described. A highly diastereoselective Pd(0)‐B(OPh)3 mediated syn‐vic‐diol formation from epoxy unsaturated ester used for the creation of C3‐C4 centres. Iodine catalyzed allylation used for synthesis of trans‐2,6‐disubstitutedtetrahydro‐2H‐Pyran. Cross‐ metathesis, Yamaguchi macrolactonization are the other key features of the synthesis.

show abstract

Section: Resultsmentioning

confidence: 99%

Studies towards the Total Synthesis of Aspergillide‐B

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Finally, an asymmetric α ‐aminoxylation of aldehydes reaction occurs in the existence of proline as the catalyst (Scheme 56). [136] …”

Section: Asymmetric Iodocyclization Reactionsmentioning

confidence: 99%

Asymmetric Synthesis of Halocyclized Products by Using Various Catalysts: A State‐of‐the‐Art Review

Dan

Sahu

et al. 2022

Eur J Org Chem

View full text Add to dashboard Cite

Halogens play a crucial part in synthetic organic chemistry. Halo‐cyclized products hold numerous applications in the pharmaceutical industries, agrochemicals, natural product synthesis, and material chemistry. Thus, this review will discuss the role of various catalysts, such as from metal‐catalysts to organocatalysts, under different conditions to synthesize various halocyclized products. The synthesis and catalytic mechanisms underlying the different asymmetric transformations will also be covered by emphasizing the enantioselectivities, diastereoselectivities, and regioselectivities from the existing pieces of literature.

show abstract

Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction

et al. 2016

Self Cite

View full text Add to dashboard Cite

A highly stereoselective formal total synthesis of brevisamide is described that proceeds through a convergent pathway and utilizes our own tandem isomerization/C–O and C–C bond formation reaction as the key step to construct the trans‐2,6‐disubstituted dihydropyran ring system. Other significant reactions in this synthesis include an iodolactonization, a Crimmins‐modified “non‐Evans” syn aldol reaction, and a Horner–Wadsworth–Emmons olefination.

show abstract

Stereoselective synthesis of the C21–C29 fragment of (+)-Sorangicin A employing iodocyclization reactions

Cited by 7 publications

References 36 publications

Studies towards the Total Synthesis of Aspergillide‐B

Studies towards the Total Synthesis of Aspergillide‐B

Asymmetric Synthesis of Halocyclized Products by Using Various Catalysts: A State‐of‐the‐Art Review

Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C–O and C–C Bond Formation Reaction

Contact Info

Product

Resources

About