Journal ArticleDOI
Concise total syntheses of (+)-strictifolione and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one.
TLDR
This work reportscise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R, 6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5, 6- dihydro-2H-pyran-2-one 2 based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions.Abstract:
Concise and efficient asymmetric total syntheses of (+)-strictifolione 1 and (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one 2 have been achieved based on the strategic application of one-pot double allylboration and ring-closing metathesis reactions. The total syntheses proceeded in only five and seven steps, respectively, from readily available 3-butenal and represent the shortest syntheses of 1 and 2 reported to date.read more
Citations
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Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses
Shichao Yu,Shengming Ma +1 more
TL;DR: This Review pays attention to the advances made in catalytic asymmetric synthesis and natural product syntheses based on well-established reactions of allenes, such as propargylation, addition, cycloaddition, cycloisomerization, cyclization, etc., with or without catalysts.
Journal ArticleDOI
Diastereoselective allylation of carbonyl compounds and imines: application to the synthesis of natural products.
TL;DR: This paper aims to demonstrate the efforts towards in-situ applicability of EMMARM, as to provide real-time information about concrete mechanical properties such as E-modulus and compressive strength.
Journal ArticleDOI
Allene in katalytischer asymmetrischer Synthese und Naturstoffsynthese
Shichao Yu,Shengming Ma +1 more
Journal ArticleDOI
Stereocontrolled Formation of Several Carbon–Carbon Bonds in Acyclic Systems
Journal ArticleDOI
Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.
Ming Chen,William R. Roush +1 more
TL;DR: 2-methyl-1,5-anti-pentenediols with either olefin geometry can be synthesized from the same allenylboronate precursor 5 in good yield and high enantioselectivity without requiring use of the BF3·OEt2 catalyst.
References
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Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
TL;DR: In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.
Journal ArticleDOI
Recent advances in olefin metathesis and its application in organic synthesis
Robert H. Grubbs,Sukbok Chang +1 more
TL;DR: In this paper, a review of recent advances in olefin metathesis focusing on the areas of ring-closing olefi cation (RCM) and cross-metathesis is presented.
Journal ArticleDOI
Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.
TL;DR: The fascinating story of olefin (or alkene) metathesis began almost five decades ago, when Anderson and Merckling reported the first carbon-carbon double-bond rearrangement reaction in the titanium-catalyzed polymerization of norbornene.
Journal ArticleDOI
Natural product synthesis using multicomponent reaction strategies.
B. Barry Touré,Dennis G. Hall +1 more
TL;DR: The preparation of urea by Wöhler constituted a landmark achievement in organic chemistry, and it laid the ground for the early days of target-oriented organic synthesis, a task deemed inconceivable by early practitioners.
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