Literature DB >> 26257916

Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Michelle H Lacoske1, Jing Xu2, Noel Mansour1, Chao Gao1, Emmanuel A Theodorakis1.   

Abstract

Herein we describe a scalable approach to the decalin moiety of maklamicin. Key to the synthesis is an intramolecular Diels-Alder (IMDA) reaction that proceeds via an endo-axial transition state to generate the desired stereochemistry. We explored the diastereoselectivity of the IMDA reaction as a function of both chiral catalysis and acyclic precursor stereochemistry.

Entities:  

Year:  2015        PMID： 26257916      PMCID： PMC4527581          DOI： 10.1039/C4QO00332B

Source DB:  PubMed          Journal:  Org Chem Front        ISSN： 2052-4110            Impact factor:   5.281


  49 in total

1.  Stereoselective synthesis of (-)-acanthoic acid.

Authors:  T Ling; B A Kramer; M A Palladino; E A Theodorakis
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

2.  On the roles of protic solvents in imidazolidinone-catalyzed transformations.

Authors:  John B Brazier; Kevin M Jones; James A Platts; Nicholas C O Tomkinson
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3.  Prevention of apoptosis by Bcl-2: release of cytochrome c from mitochondria blocked.

Authors:  J Yang; X Liu; K Bhalla; C N Kim; A M Ibrado; J Cai; T I Peng; D P Jones; X Wang
Journal:  Science       Date:  1997-02-21       Impact factor: 47.728

Review 4.  Natural products containing 'decalin' motif in microorganisms.

Authors:  Gang Li; Souvik Kusari; Michael Spiteller
Journal:  Nat Prod Rep       Date:  2014-09       Impact factor: 13.423

5.  Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326.

Authors:  Jae-Hyuk Jang; Yukihiro Asami; Jun-Pil Jang; Sun-Ok Kim; Dong Oh Moon; Kee-Sun Shin; Daisuke Hashizume; Makoto Muroi; Tamio Saito; Hyuncheol Oh; Bo Yeon Kim; Hiroyuki Osada; Jong Seog Ahn
Journal:  J Am Chem Soc       Date:  2011-04-18       Impact factor: 15.419

6.  Catalytic asymmetric carbon-carbon bond formation via allylic alkylations with organolithium compounds.

Authors:  Manuel Pérez; Martín Fañanás-Mastral; Pieter H Bos; Alena Rudolph; Syuzanna R Harutyunyan; Ben L Feringa
Journal:  Nat Chem       Date:  2011-03-13       Impact factor: 24.427

7.  Elucidation of the kijanimicin gene cluster: insights into the biosynthesis of spirotetronate antibiotics and nitrosugars.

Authors:  Hua Zhang; Jess A White-Phillip; Charles E Melançon; Hyung-jin Kwon; Wei-luen Yu; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

8.  Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses.

Authors:  Audrey Caravano; Robert A Field; Jonathan M Percy; Giuseppe Rinaudo; Ricard Roig; Kuldip Singh
Journal:  Org Biomol Chem       Date:  2009-01-23       Impact factor: 3.876

9.  A novel catalytic asymmetric route towards skipped dienes with a methyl-substituted central stereogenic carbon.

Authors:  Yange Huang; Martín Fañanás-Mastral; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Commun (Camb)       Date:  2013-04-25       Impact factor: 6.222

10.  Intramolecular Diels-Alder reactions of cycloalkenones: stereoselectivity, Lewis acid acceleration, and halogen substituent effects.

Authors:  Hung V Pham; Robert S Paton; Audrey G Ross; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419
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