Literature DB >> 18549226

Formal total synthesis of RK-397 via an asymmetric hydration and iterative allylation strategy.

Haibing Guo1, Matthew S Mortensen, George A O'Doherty.   

Abstract

A formal total synthesis of the oxopentaene macrolide antibiotic RK-397 has been achieved. Nine stereocenters were established by a combination of allylation and our asymmetric hydration reactions and a 1,5 anti-selective aldol reaction. The synthesis proceeded in 19 steps from simple achiral conjugated dienoates.

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Year:  2008        PMID： 18549226     DOI： 10.1021/ol801055b

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


  9 in total

1.  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

2.  Total synthesis of (+)-roxaticin via C-C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles in polyketide construction.

Authors:  Soo Bong Han; Abbas Hassan; In Su Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

3.  Total and Formal Syntheses of Fostriecin.

Authors:  Gao Dong; Bohui Li; George O'Doherty
Journal:  Org Chem Front       Date:  2020-10-12       Impact factor: 5.281

Review 4.  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

5.  De Novo Asymmetric Syntheses of (+)-Goniothalamin, (+)-Goniothalamin oxide and 7,8-Bis-epi-Goniothalamin using Asymmetric Allylations.

Authors:  Philip Harsh; George A O'Doherty
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

Review 6.  Synthesis and biological study of the phomopsolide and phomopsolidone natural products.

Authors:  Alhanouf Z Aljahdali; Kathryn A Foster; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2020-10-07       Impact factor: 6.222

7.  1,n-glycols as dialdehyde equivalents in iridium-catalyzed enantioselective carbonyl allylation and iterative two-directional assembly of 1,3-polyols.

Authors:  Yu Lu; In Su Kim; Abbas Hassan; David J Del Valle; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship.

Authors:  Yanping Wang; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419

9.  Approach to the Synthesis of the C1-C11 and C14-C18 portion of Leucascandrolide A.

Authors:  T J Hunter; J Zheng; G A O'Doherty
Journal:  Org Chem Front       Date:  2016-07-12       Impact factor: 5.281
  9 in total

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