Literature DB >> 15493903

Remote asymmetric induction with vinylketene silyl n,o-acetal.

Shin-Ichi Shirokawa1, Masato Kamiyama, Tomoaki Nakamura, Masakazu Okada, Atsuo Nakazaki, Seijiro Hosokawa, Susumu Kobayashi.   

Abstract

A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of controlling remote asymmetric induction. The methyl group at the alpha-position is important in achieving a high level of stereoselectivity. From a synthetic point of view, this methodology can provide a one-step construction of delta-hydroxy-alpha,gamma-dimethyl-alpha,beta-unsaturated carbonyl unit that is seen in many natural polyketide products.

Entities:  

Year:  2004        PMID： 15493903     DOI： 10.1021/ja0465855

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


  17 in total

1.  Concise route to defined stereoisomers of the hydroxy acid of the chondramides.

Authors:  Anke Schmauder; Sven Müller; Martin E Maier
Journal:  Tetrahedron       Date:  2008-06-30       Impact factor: 2.457

2.  Synthesis and structure-activity relationship study of FD-891: importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells.

Authors:  Tomohiro Itagaki; Ayano Kawamata; Miho Takeuchi; Keisuke Hamada; Yoshiharu Iwabuchi; Tadashi Eguchi; Fumitaka Kudo; Takeo Usui; Naoki Kanoh
Journal:  J Antibiot (Tokyo)       Date:  2016-01-27       Impact factor: 2.649

3.  Total synthesis and structure revision of the marine metabolite palmerolide A.

Authors:  Xin Jiang; Bo Liu; Sylvain Lebreton; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2007-04-26       Impact factor: 15.419

4.  De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

Authors:  Md Moinuddin Ahmed; Matthew S Mortensen; George A O'Doherty
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

Review 5.  De novo synthesis of natural products via the asymmetric hydration of polyenes.

Authors:  Yanping Wang; Yalan Xing; Qi Zhang; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2011-05-11       Impact factor: 6.222

Review 6.  Challenges and discoveries in the total synthesis of complex polyketide natural products.

Authors:  Ian Paterson; Nelson Yuen Sum Lam
Journal:  J Antibiot (Tokyo)       Date:  2017-10-25       Impact factor: 2.649

7.  New chiral synthons for efficient introduction of bispropionates via stereospecific oxonia-cope rearrangements.

Authors:  Yi-Hung Chen; Frank E McDonald
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

8.  Synthesis of ent-BE-43547A1 reveals a potent hypoxia-selective anticancer agent and uncovers the biosynthetic origin of the APD-CLD natural products.

Authors:  Nikolaj L Villadsen; Kristian M Jacobsen; Ulrik B Keiding; Esben T Weibel; Bjørn Christiansen; Thomas Vosegaard; Morten Bjerring; Frank Jensen; Mogens Johannsen; Thomas Tørring; Thomas B Poulsen
Journal:  Nat Chem       Date:  2016-11-21       Impact factor: 24.427

9.  Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

10.  Total synthesis of piericidin A1. Application of a modified Negishi carboalumination-nickel-catalyzed cross-coupling.

Authors:  Bruce H Lipshutz; Benjamin Amorelli
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419
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