Torsional Steering Controls the Stereoselectivity of Epoxidation in the Guanacastepene A Synthesis-Reference-Cited by-同舟云学术

Torsional Steering Controls the Stereoselectivity of Epoxidation in the Guanacastepene A Synthesis

Published:2006-03-21 Issue:8 Volume:8 Page:1513-1516
ISSN:1523-7060
Container-title:Organic Letters
language:en
Short-container-title:Org. Lett.

Author:

Cheong Paul Ha-Yeon¹,Yun Heedong¹,Danishefsky Samuel J.¹,Houk K. N.¹

Affiliation:

1. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, and Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/ol052862g

Reference20 articles.

1. A Stereoselective Route to Guanacastepene A through a Surprising Epoxidation This work was supported by the National Institutes of Health (CA-28824). S.L. is a US Army breast cancer research program postdoctoral fellow (DAMD-17-99-1-9373). G.B.D. is an NIH postdoctoral fellow (1 F32 NS11150-01). D.S.T. is a Damon Runyon Cancer Research Foundation postdoctoral fellow (DRG-1641). We thank Dr. George Sukenick and Sylvi Rusli (NMR Core Facility, CA-02848) for mass spectral analyses.

2. Probing the formation and chemistry of enoxyoxirane derivatives in the C-ring en route to guanacastepene

3. Origin of Huisgen's factor x: staggering of allylic bonds promotes anomalously rapid exo attack on norbornenes

4. Quantitative modeling of proximity effects on organic reactivity

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