Literature DB >> 26323232

Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

Andrés Villalpando1, Mirza A Saputra, Thomas H Tugwell, Rendy Kartika.   

Abstract

We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 26323232      PMCID： PMC4599979          DOI： 10.1039/c5cc06365e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

1.  The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles.

Authors:  Jonathan W Burton; Edward A Anderson; Paul T O'Sullivan; Ian Collins; John E Davies; Andrew D Bond; Neil Feeder; Andrew B Holmes
Journal:  Org Biomol Chem       Date:  2008-01-04       Impact factor: 3.876

2.  Total synthesis of leustroducsin B.

Authors:  Kazuyuki Miyashita; Tomoyuki Tsunemi; Takafumi Hosokawa; Masahiro Ikejiri; Takeshi Imanishi
Journal:  J Org Chem       Date:  2008-06-13       Impact factor: 4.354

3.  Asymmetric total synthesis of (+)-danicalipin A.

Authors:  Takehiko Yoshimitsu; Ryo Nakatani; Akihiro Kobayashi; Tetsuaki Tanaka
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

4.  Synthesis of undecachlorosulfolipid A: re-evaluation of the nominal structure.

Authors:  Christian Nilewski; Nicholas R Deprez; Thomas C Fessard; Dong Bo Li; Roger W Geisser; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-08       Impact factor: 15.336

Review 5.  Chlorosulfolipids: structure, synthesis, and biological relevance.

Authors:  D Karl Bedke; Christopher D Vanderwal
Journal:  Nat Prod Rep       Date:  2010-12-02       Impact factor: 13.423

6.  Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation.

Authors:  Caitlan E Ayala; Andres Villalpando; Alex L Nguyen; Gregory T McCandless; Rendy Kartika
Journal:  Org Lett       Date:  2012-07-10       Impact factor: 6.005

7.  Enantioselective dichlorination of allylic alcohols.

Authors:  K C Nicolaou; Nicholas L Simmons; Yongcheng Ying; Philipp M Heretsch; Jason S Chen
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

8.  Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors:  Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal:  Nature       Date:  2009-01-29       Impact factor: 49.962

9.  Stereoselective dichlorination of allylic alcohol derivatives to access key stereochemical arrays of the chlorosulfolipids.

Authors:  Grant M Shibuya; Jacob S Kanady; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2008-08-22       Impact factor: 15.419

10.  General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

Authors:  Won-jin Chung; Joseph S Carlson; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2014-02-13       Impact factor: 4.354
View more
  3 in total

1.  A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.

Authors:  Sharon E Michalak; Sangkil Nam; David M Kwon; David A Horne; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

2.  A decade review of triphosgene and its applications in organic reactions.

Authors:  Moshood O Ganiu; Binod Nepal; Joshua P Van Houten; Rendy Kartika
Journal:  Tetrahedron       Date:  2020-09-06       Impact factor: 2.457

3.  Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy.

Authors:  Tomoki Itoh; Yuusuke Chiba; Shunsuke Kawaguchi; Yuki Koitaya; Yuuma Yoneta; Koji Yamada; Takumi Abe
Journal:  RSC Adv       Date:  2019-04-03       Impact factor: 4.036
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.