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Literature DB >> 17002354

Enantioselective synthesis of gamma-hydroxyenones by chiral base-catalyzed Kornblum DeLaMare rearrangement.

Steven T Staben¹, Xin Linghu, F Dean Toste.

Abstract

A cinchona-alkaloid catalyzed asymmetric Kornblum DeLaMare rearrangement has been developed. Thus, enantioenriched 4-hydroxyenones are prepared from dienes by a two-step sequence involving photochemical dioxygenation and chiral base-catalyzed desymmetrization of the resulting endoperoxides.

Entities: Chemical

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Year: 2006 PMID： 17002354 DOI： 10.1021/ja065464x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

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Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents.

Authors: K C Nicolaou; Min Lu; Sotirios Totokotsopoulos; Philipp Heretsch; Denis Giguère; Ya-Ping Sun; David Sarlah; Thu H Nguyen; Ian C Wolf; Donald F Smee; Craig W Day; Selina Bopp; Elizabeth A Winzeler
Journal: J Am Chem Soc Date: 2012-10-04 Impact factor: 15.419

3. Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine.

Authors: K C Nicolaou; Stephan Rigol
Journal: Nat Prod Rep Date: 2020-04-22 Impact factor: 13.423

10. Ground-state dioxygen undergoes metal-free [3 + 2]-annulations with allenes and nitrosoarenes under ambient conditions.

Authors: Jinxian Liu; Manisha Skaria; Pankaj Sharma; Yun-Wei Chiang; Rai-Shung Liu
Journal: Chem Sci Date: 2017-05-24 Impact factor: 9.825

10 in total

Enantioselective synthesis of gamma-hydroxyenones by chiral base-catalyzed Kornblum DeLaMare rearrangement.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

3. Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine.

Review 4. Rearrangements of organic peroxides and related processes.

5. Total synthesis of epicoccin G.

6. Highly efficient C(CO)-C(alkyl) bond cleavage in ketones to access esters over ultrathin N-doped carbon nanosheets.

7. Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration.

8. Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis.

9. Probing the reactivity of singlet oxygen with purines.

10. Ground-state dioxygen undergoes metal-free [3 + 2]-annulations with allenes and nitrosoarenes under ambient conditions.