Literature DB >> 17958434

A highly E-stereoselective approach to beta-iodo Morita-Baylis-Hillman esters: synthesis of secokotomolide A.

Sung Il Lee1, Geum-Sook Hwang, Su Cheol Shin, Tae Gyo Lee, Ran Hee Jo, Do Hyun Ryu.   

Abstract

A geometric-selective synthesis of (E)-beta-iodo Morita-Baylis-Hillman esters has been developed through a three-component aldol-type reaction using BF3.Et2O and TMS-I. The synthetic utility of the (E)-beta-iodo Morita-Baylis-Hillman esters was demonstrated in the first reported short synthesis of secokotomolide A.

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Year:  2007        PMID： 17958434     DOI： 10.1021/ol702134w

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


  3 in total

1.  Efficient assembly of 2,5,6-substituted pyrimidines via MgI(2)-mediated Morita-Baylis-Hillman reaction.

Authors:  Vasudha Sharma; Mark L McLaughlin
Journal:  J Comb Chem       Date:  2010-05-10

2.  Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors:  Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

3.  A macrocyclic β-iodoallenolate intermediate is key: synthesis of the ABD core of phomactin A.

Authors:  Jennifer Ciesielski; Kevin Cariou; Alison J Frontier
Journal:  Org Lett       Date:  2012-08-02       Impact factor: 6.005
  3 in total

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