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Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction
Journal article   Open access   Peer reviewed

Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction

Barry B Snider and Jingye Zhou
Organic letters, Vol.8(7), pp.1283-1286
03/01/2006
DOI: https://doi.org/10.1021/ol052948+
PMCID: PMC2543932
PMID: 16562872

Abstract

Mixtures Macrocyclic compounds Ethers Lactones Stereochemistry
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/CDCl3 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.
url
https://doi.org/10.1021/ol052948+View
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