Literature DB >> 19873991

Formal total synthesis of (-)-saliniketals.

J S Yadav1, Sk Samad Hossain, Madasu Madhu, Debendra K Mohapatra.   

Abstract

A highly stereoselective formal total synthesis of the ornithine decarboxylase inhibitors (-)-saliniketals A and B is described. The salient features of the synthesis are the utilization of a desymmetrization technique to create six contiguous chiral centers from a single bicyclic precursor as well as substrate-controlled Grignard reaction, intramolecular Wacker-type oxidation, and antialdol reaction following Pirrung-Heathcock conditions.

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Year:  2009        PMID： 19873991     DOI： 10.1021/jo901913h

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


  5 in total

1.  Shared biosynthesis of the saliniketals and rifamycins in Salinispora arenicola is controlled by the sare1259-encoded cytochrome P450.

Authors:  Micheal C Wilson; Tobias A M Gulder; Taifo Mahmud; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2010-09-15       Impact factor: 15.419

2.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

3.  Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Authors:  Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

Review 4.  The marine actinomycete genus Salinispora: a model organism for secondary metabolite discovery.

Authors:  Paul R Jensen; Bradley S Moore; William Fenical
Journal:  Nat Prod Rep       Date:  2015-05       Impact factor: 13.423

5.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419
  5 in total

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