Literature DB >> 16562872

Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.

Barry B Snider1, Jingye Zhou.   

Abstract

[reaction: see text] The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl(3) provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.

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Year:  2006        PMID： 16562872      PMCID： PMC2543932          DOI： 10.1021/ol052948+

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


  12 in total

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