Literature DB >> 18461955

Asymmetric total synthesis of (+)-phoslactomycin B.

Setsuya Shibahara1, Masataka Fujino, Yasumasa Tashiro, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama.   

Abstract

(+)-Phoslactomycin B was synthesized by a highly enantio- and stereoselective approach involving asymmetric pentenylation, Suzuki-Miyaura coupling, ring-closing metathesis, asymmetric dihydroxylation, and Stille coupling. The synthetic method developed enables us to synthesize three other isomers concerning the C11-OH and Delta12-double bond.

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Year:  2008        PMID： 18461955     DOI： 10.1021/ol8004672

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

Authors:  Barry M Trost; Joshua D Knopf; Cheyenne S Brindle
Journal:  Chem Rev       Date:  2016-12-08       Impact factor: 60.622

2.  Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.

Authors:  Dong Gao; George A O'Doherty
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

Review 3.  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

4.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

5.  Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-05-17       Impact factor: 6.005

6.  Total synthesis and evaluation of phostriecin and key structural analogues.

Authors:  Christopher P Burke; Mark R Swingle; Richard E Honkanen; Dale L Boger
Journal:  J Org Chem       Date:  2010-07-29       Impact factor: 4.354

7.  Total synthesis, assignment of the relative and absolute stereochemistry, and structural reassignment of phostriecin (aka Sultriecin).

Authors:  Christopher P Burke; Nadia Haq; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419

8.  A Highly Convergent Total Synthesis of Leustroducsin B.

Authors:  Barry M Trost; Berenger Biannic; Cheyenne S Brindle; B Michael O'Keefe; Thomas J Hunter; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2015-09-01       Impact factor: 15.419

9.  Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes.

Authors:  Bryony L Elbert; Diane S W Lim; Haraldur G Gudmundsson; Jack A O'Hanlon; Edward A Anderson
Journal:  Chemistry       Date:  2014-06-04       Impact factor: 5.236
  9 in total

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