Literature DB >> 21076637

Synthesis of a Tricyclic Core of Rameswaralide.

Barry M Trost1, Hien M Nguyen, Christopher Koradin.   

Abstract

A tricyclic core containing a 5,7-fused bicyclic unit of rameswaralide was prepared starting from a 1,6-enyne. The synthetic sequence involved (i) ruthenium-catalyzed [5+2]-cycloaddition of 1,6-enyne, (ii) an acyl radical based approach to construct the lactone, and (iii) a regioselective installation of the conjugated double bond by a concomitant sulfenylation-dehydrosulfenylation sequence.

Entities:  

Year:  2010        PMID： 21076637      PMCID： PMC2976576          DOI： 10.1016/j.tetlet.2010.09.042

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  Constructing Tricyclic Compounds Containing a Seven-Membered Ring by Ruthenium-Catalyzed Intramolecular

Authors:  Barry M. Trost; Hong C. Shen
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-18       Impact factor: 15.336

2.  Synthetic approaches to guanacastepenes. Enantiospecific syntheses of BC and AB ring systems of guanacastepenes and rameswaralide.

Authors:  A Srikrishna; Dattatraya H Dethe
Journal:  Org Lett       Date:  2004-01-22       Impact factor: 6.005

3.  Asymmetric catalysis of the [5 + 2] cycloaddition reaction of vinylcyclopropanes and pi-systems.

Authors:  Paul A Wender; Lars O Haustedt; Jaehong Lim; Jennifer A Love; Travis J Williams; Joo-Yong Yoon
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

4.  A metal-catalyzed intermolecular [5+2] cycloaddition/Nazarov cyclization sequence and cascade.

Authors:  Paul A Wender; René T Stemmler; Lauren E Sirois
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

5.  Electronic and steric control of regioselectivities in Rh(I)-catalyzed (5 + 2) cycloadditions: experiment and theory.

Authors:  Peng Liu; Lauren E Sirois; Paul Ha-Yeon Cheong; Zhi-Xiang Yu; Ingo V Hartung; Heiko Rieck; Paul A Wender; K N Houk
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

6.  Syntheses of seven-membered rings: ruthenium-catalyzed intramolecular [5+2] cycloadditions.

Authors:  Barry M Trost; Hong C Shen; Daniel B Horne; F Dean Toste; Bernhard G Steinmetz; Christopher Koradin
Journal:  Chemistry       Date:  2005-04-08       Impact factor: 5.236

7.  Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+2] cycloaddition.

Authors:  Barry M Trost; Yimin Hu; Daniel B Horne
Journal:  J Am Chem Soc       Date:  2007-08-31       Impact factor: 15.419

8.  On the diastereoselectivity of ru-catalyzed [5 + 2] cycloadditions.

Authors:  Barry M Trost; Hong C Shen; Tobias Schulz; Christopher Koradin; Hartmut Schirok
Journal:  Org Lett       Date:  2003-10-30       Impact factor: 6.005

9.  Substituent effects, reactant preorganization, and ligand exchange control the reactivity in Rh(I)-catalyzed (5+2) cycloadditions between vinylcyclopropanes and alkynes.

Authors:  Peng Liu; Paul Ha-Yeon Cheong; Zhi-Xiang Yu; Paul A Wender; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 + 2) cycloaddition reactions with vinylcyclopropanes.

Authors:  Zhi-Xiang Yu; Paul Ha-Yeon Cheong; Peng Liu; Claude Y Legault; Paul A Wender; K N Houk
Journal:  J Am Chem Soc       Date:  2008-02-02       Impact factor: 15.419
  10 in total
  8 in total

1.  Studies toward the synthesis of maoecrystal V.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

3.  Bridging the gap between natural product synthesis and drug discovery.

Authors:  Nathanyal J Truax; Daniel Romo
Journal:  Nat Prod Rep       Date:  2020-10-26       Impact factor: 13.423

Review 4.  Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-05-18       Impact factor: 60.622

5.  Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores.

Authors:  Nathanyal J Truax; Safiat Ayinde; Khoi Van; Jun O Liu; Daniel Romo
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

6.  Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Authors:  Xing-zhong Shu; Casi M Schienebeck; Xiaoxun Li; Xin Zhou; Wangze Song; Lianqing Chen; Ilia A Guzei; Weiping Tang
Journal:  Org Lett       Date:  2015-10-06       Impact factor: 6.005

7.  3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.

Authors:  Casi M Schienebeck; Xiaoxun Li; Xing-Zhong Shu; Weiping Tang
Journal:  Pure Appl Chem       Date:  2014-03-01       Impact factor: 2.453

Review 8.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622
  8 in total

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