Journal ArticleDOI
Convergent synthesis of polyether ionophore antibiotics: the synthesis of the monensin bis(tetrahydrofuran) via the Claisen rearrangement of an ester enolate with a .beta.-leaving group
Robert E. Ireland,D. W. Norbeck +1 more
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This article is published in Journal of the American Chemical Society.The article was published on 1985-05-01. It has received 72 citations till now. The article focuses on the topics: Claisen rearrangement & Convergent synthesis.read more
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Journal ArticleDOI
Synthetic routes to tetrahydrofuran, tetrahydropyran, and spiroketal units of polyether antibiotics and a survey of spiroketals of other natural products
TL;DR: In this paper, a review of the stereocontrolled methods by which these fragments have been prepared for polyether sythesis and includes a survey of routes to spiroketals of other natural products.
Journal ArticleDOI
Strategy and methodology development for the total synthesis of polyether ionophore antibiotics.
Book ChapterDOI
7.2 – Claisen Rearrangements
TL;DR: In this paper, a survey of variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis is presented, highlighting the influence of steric and electronic parameters on transition state geometries.
Journal ArticleDOI
(+)-11,11′-Di-O-methylelaiophylidene – preparation from elaiophylin and total synthesis from (R)-3-hydroxybutyrate and (S)-malate
Dieter Seebach,Hak-Fun Chow,Richard F. W. Jackson,Marius A. Sutter,Suvit Thaisrivongs,Jürg Zimmermann +5 more
TL;DR: In this article, a C2-symmetrical macrodiolide with 2 × 11 stereogenic units was synthesized from (R)-3-hydroxy-butanoate (from the biopolymer PHB) and (S)-malic ester, using diastereoselective steps for the generation of the other stereogenic unit.
Journal ArticleDOI
Total Synthesis of (−)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol.
Ian Paterson,Michael V. Perkins +1 more
TL;DR: In this article, the total synthesis of (−)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9.