Literature DB >> 23126440

Total synthesis of (±)-maoecrystal V.

Feng Peng1, Samuel J Danishefsky.   

Abstract

The total synthesis of racemic maoecrystal V has been accomplished. Key steps include an intramolecular Diels-Alder cyclization to rapidly construct the core system from simple starting materials and the creation of the A-C ring trans-fusion through intramolecular delivery of a hydrogen to the hindered β-face of the ring system.

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Year:  2012        PMID： 23126440      PMCID： PMC3512084          DOI： 10.1021/ja309905j

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


  26 in total

1.  Total synthesis of (±) maoecrystal V.

Authors:  Jianxian Gong; Guang Lin; Wenbo Sun; Chuang-Chuang Li; Zhen Yang
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

2.  Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

Review 3.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

4.  Synthesis of an advanced maoecrystal V core structure.

Authors:  Lin Dong; Lujiang Deng; Yee Hwee Lim; Gulice Y C Leung; David Y-K Chen
Journal:  Chemistry       Date:  2011-04-13       Impact factor: 5.236

5.  A synthesis of the carbocyclic core of maoecrystal V.

Authors:  Kiel E Lazarski; Dennis X Hu; Charlotte L Stern; Regan J Thomson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

6.  Studies on the total synthesis of steroidal antibiotics. I. An efficient, stereoselective method for the formation of trans-syn-trans-perhydrophenanthrene derivatives.

Authors:  R E Ireland; U Hengartner
Journal:  J Am Chem Soc       Date:  1972-05-17       Impact factor: 15.419

7.  Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine.

Authors:  E J Corey; Takanori Shibata; Thomas W Lee
Journal:  J Am Chem Soc       Date:  2002-04-17       Impact factor: 15.419

8.  The total synthesis of (+/-)-merrilactone A.

Authors:  Vladimir B Birman; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

9.  Facile synthesis of cis-2-Alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols.

Authors:  Michael E Jung; Damian A Allen
Journal:  Org Lett       Date:  2008-04-23       Impact factor: 6.005

10.  A synthesis of the carbon skeleton of maoecrystal V.

Authors:  Paul J Krawczuk; Niklas Schöne; Phil S Baran
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005
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  12 in total

1.  Pattern recognition analysis in complex molecule synthesis and the preparation of iso-Diels-Alder motifs.

Authors:  Feng Peng; Robin E Grote; Rebecca M Wilson; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-19       Impact factor: 11.205

2.  Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.

Authors:  Aneta Turlik; Yifeng Chen; Anthony C Scruse; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2019-05-07       Impact factor: 15.419

3.  Ideality in Context: Motivations for Total Synthesis.

Authors:  David S Peters; Cody Ross Pitts; Kyle S McClymont; Thomas P Stratton; Cheng Bi; Phil S Baran
Journal:  Acc Chem Res       Date:  2021-01-21       Impact factor: 22.384

4.  Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

Authors:  Ping Lu; Zhenhua Gu; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2013-09-23       Impact factor: 15.419

Review 5.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

6.  Hydromethylation of Unactivated Olefins.

Authors:  Hai T Dao; Chao Li; Quentin Michaudel; Brad D Maxwell; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

7.  Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.

Authors:  Ping Lu; Artur Mailyan; Zhenhua Gu; David M Guptill; Hengbin Wang; Huw M L Davies; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2014-12-11       Impact factor: 15.419

8.  Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton.

Authors:  Amy M Hamlin; David Lapointe; Kyle Owens; Richmond Sarpong
Journal:  J Org Chem       Date:  2014-07-11       Impact factor: 4.354

Review 9.  The synthesis of functionalized bridged polycycles via C-H bond insertion.

Authors:  Jiun-Le Shih; Po-An Chen; Jeremy A May
Journal:  Beilstein J Org Chem       Date:  2016-05-17       Impact factor: 2.883

10.  11-Step Total Synthesis of (-)-Maoecrystal V.

Authors:  Artiom Cernijenko; Rune Risgaard; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-07-26       Impact factor: 15.419
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