Literature DB >> 29786446

Total Synthesis of the Marine Phosphomacrolide, (-)-Enigmazole A, Exploiting Multicomponent Type I Anion Relay Chemistry (ARC) in Conjunction with a Late-Stage Petasis-Ferrier Union/Rearrangement.

Yanran Ai1, Mariya V Kozytska1, Yike Zou1, Anton S Khartulyari1, William A Maio1, Amos B Smith1.   

Abstract

An effective late-stage large-fragment union/rearrangement exploiting the Petasis-Ferrier protocol, in conjunction with multicomponent Type I Anion Relay Chemistry (ARC) to access advanced intermediates, permits completion of a convergent, stereocontrolled total synthesis of the architecturally complex phosphomacrolide (-)-enigmazole A (1).

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Year:  2018        PMID： 29786446      PMCID： PMC5984197          DOI： 10.1021/acs.joc.8b00899

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

1.  Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Authors:  Amos B Smith; Ming Xian
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

2.  Total synthesis of (-)-okilactomycin.

Authors:  Amos B Smith; Kallol Basu; Todd Bosanac
Journal:  J Am Chem Soc       Date:  2007-11-13       Impact factor: 15.419

3.  Isolation, structural elucidation, and absolute stereochemistry of enigmazole A, a cytotoxic phosphomacrolide from the Papua New Guinea marine sponge Cinachyrella enigmatica.

Authors:  Naoya Oku; Kentaro Takada; Richard W Fuller; Jennifer A Wilson; Megan L Peach; Lewis K Pannell; James B McMahon; Kirk R Gustafson
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

4.  Total synthesis of enigmazole A from Cinachyrella enigmatica. Bidirectional bond constructions with an ambident 2,4-disubstituted oxazole synthon.

Authors:  Colin K Skepper; Tim Quach; Tadeusz F Molinski
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

5.  Mechanistic studies of highly enantio- and diastereoselective aza-Petasis-Ferrier rearrangement catalyzed by chiral phosphoric acid.

Authors:  Masahiro Terada; Takazumi Komuro; Yasunori Toda; Toshinobu Korenaga
Journal:  J Am Chem Soc       Date:  2014-05-01       Impact factor: 15.419

6.  Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes.

Authors:  Masahiro Terada; Yasunori Toda
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

7.  Evolution of the Petasis-Ferrier union/rearrangement tactic: construction of architecturally complex natural products possessing the ubiquitous cis-2,6-substituted tetrahydropyran structural element.

Authors:  Amos B Smith; Richard J Fox; Thomas M Razler
Journal:  Acc Chem Res       Date:  2008-05       Impact factor: 22.384

8.  Gold(I)-Catalyzed Hydroaminaloxylation and Petasis-Ferrier Rearrangement Cascade of Aminaloalkynes.

Authors:  Amol B Gade; Nitin T Patil
Journal:  Org Lett       Date:  2016-03-30       Impact factor: 6.005

9.  DFT study on the mechanism and stereochemistry of the Petasis-Ferrier rearrangements.

Authors:  Guo-Jie Jiang; Yi Wang; Zhi-Xiang Yu
Journal:  J Org Chem       Date:  2013-07-03       Impact factor: 4.354

10.  Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419
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  2 in total

1.  Total Synthesis of (-)-Bastimolide A: A Showcase for Type I Anion Relay Chemistry.

Authors:  Joshua B Cox; Alex A Kellum; Yiwen Zhang; Bo Li; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-24       Impact factor: 16.823

2.  Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.

Authors:  Kevin T O'Brien; Amos B Smith
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005
  2 in total

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