Synthetic Studies on (12S)-12-Hydroxymonocerin

2014 ◽  
Vol 1035 ◽  
pp. 111-117
Author(s):  
Jun Peng Li ◽  
Han Yang ◽  
Jia Lin Chen ◽  
Qing Feng Xiong ◽  
Hao Cui ◽  
...  
Keyword(s):  
Novel Approach ◽  
Synthetic Studies ◽  
Key Steps

A novel approach to assemble the (12S)-12-Hydroxymonocerin’s core skeleton was developed in 29% overall yield, in which a three component Linchpin coupling, stereocontrolled reduction and an intramolecular Friedel-Crafts/Marson cyclization were utilized as key steps.

Synthesis of Multi-Substituted Bicycloalkyl Boronates: An Intramolecular Coupling Approach to Alkyl Bioisosteres

2021 ◽  
Author(s):  
Yangyang Yang ◽  
Jet Tsien ◽  
Jonathan Hughes ◽  
Byron Peters ◽  
Rohan Merchant ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Material Chemistry ◽  
Novel Approach ◽  
Coupling Approach ◽  
New Type ◽  
Strain Release ◽  
Synthetic Studies ◽  
Bicyclic Molecules

<p>Bicyclic hydrocarbons, bicyclo[1.1.1]pentanes (BCPs) in particular, play an emerging role as saturated bioisosteres in pharmaceutical, agrochemical, and material chemistry. Taking advantage of strain release strategies, prior synthetic studies have featured the synthesis of bridgehead-substituted (C1, C3) BCPs from [1.1.1]propellane. This work describes a novel approach to accessing multi-substituted BCPs via a new type of intramolecular cyclization. In addition to the C1, C3-disubstituted BCPs, this method also enables the construction of yet underexplored tri-substituted (C1, C2 and C3) BCPs from readily accessible cyclobutanones. The broad generality of this cyclization is examined through synthesis of a variety of caged bicyclic molecules, ranging from [1.1.1] to [3.2.1] scaffolds. The modularity afforded by the pendant bridgehead Bpin resulted from the cyclization is demonstrated via several downstream functionalizations, highlighting the ability of this approach for programmed and divergent synthesis of multi-substituted bicyclic hydrocarbons.<br></p>

Synthetic Studies toward Diazonamide A. A Novel Approach for Polyoxazole Synthesis

2001 ◽  
Vol 3 (9) ◽  
pp. 1261-1264 ◽  
Author(s):  
Peter Wipf ◽  
Joey-Lee Methot
Keyword(s):  
Diazonamide A ◽  
Novel Approach ◽  
Synthetic Studies

Enantioselective total synthesis of (S)-nakinadine B

RSC Advances ◽  
2016 ◽  
Vol 6 (31) ◽  
pp. 25913-25917 ◽  
Author(s):  
Yuvraj Garg ◽  
Satyendra Kumar Pandey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Michael Addition ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Novel Approach ◽  
Key Steps

A novel approach for the synthesis of (S)-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.

Synthetic Studies on Viridin Skeleton through Regio- and Stereoselective Functionalization of the AE-Ring Moiety

Synlett ◽  
2021 ◽  
Author(s):  
Shuhei Hori ◽  
Sho Ishida ◽  
Go Ito ◽  
Koji Sugiyama ◽  
Chiharu Yuki ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Ring Structure ◽  
Diels Alder ◽  
Furan Derivative ◽  
Epoxide Opening ◽  
Synthetic Studies ◽  
Stereoselective Epoxidation ◽  
Key Steps ◽  
Alder Adduct

4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin and equipped with required substituents on the A-ring, were synthesized via the Diels-Alder adduct of a furan derivative and maleic anhydride with high regio- and stereoselectivities. The key steps of this work include the regioselective opening of the tetrahydrofuran, stereoselective epoxidation, and AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.

scholarly journals Synthetic Studies of Enacyloxins: A Series of Antibiotics Isolated from Frateuria sp. W-315: C1′-C8′ and C9′-C15′ Fragments

2015 ◽  
Vol 10 (4) ◽  
pp. 1934578X1501000
Author(s):  
Aki Saito ◽  
Wataru Igarashi ◽  
Hiroyuki Furukawa ◽  
Hiroki Hoshikawa ◽  
Teiko Yamada ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Synthetic Studies ◽  
Wittig Reactions ◽  
Key Steps

Synthetic studies of enacyloxins (ENXs), a series of yellow-colored, polyene-polyol antibiotics produced by Frateuria sp. W-315, are described. The C1′-C8′ polyene fragments were prepared using successive Wittig reactions. The C9′-C15′ and C10′-C15′ fragments were constructed from ( S)-isopropylideneglyceraldehyde using Yamaguchi's nucleophilic substitution reaction of acetylide to epoxide, and/or Marshall's allenylindium mediated reaction as the key steps.

Synthetic studies towards bruceantin. Part 2. The synthesis of a pentacyclic intermediate

1991 ◽  
Vol 69 (4) ◽  
pp. 723-731 ◽  
Author(s):  
Sultan Darvesh ◽  
Andrew S. Grant ◽  
David I. MaGee ◽  
Zdenek Valenta
Keyword(s):  
Key Words ◽  
Michael Reaction ◽  
Sigmatropic Rearrangement ◽  
Synthetic Approach ◽  
Forming Strategy ◽  
Acid Catalyzed ◽  
Synthetic Studies ◽  
Key Steps

In a synthetic approach to the quassinoid bruceantin (2), the key intermediate 8 obtained via alkylation of a dianion has been transformed into the pentacyclic intermediate 33 via an ABDC ring forming strategy. The key steps involved in this route are as follows: a unique acid catalyzed cyclization, 19 → 20; an intramolecular Michael reaction, 24 → 28; and an allyl sulfoxide [2,3]-sigmatropic rearrangement to introduce the axial C12 alcohol, 31 → 33. Key words: bruceantin, quassinoids, cyclization, sulfoxides, sigmatropic rearrangement.

Synthetic studies of callyspongiolide: synthesis of the macrolactone core of the molecule

2016 ◽  
Vol 14 (28) ◽  
pp. 6769-6779 ◽  
Author(s):  
Sudhakar Athe ◽  
Ashish Sharma ◽  
Kanakaraju Marumudi ◽  
Subhash Ghosh
Keyword(s):  
Natural Product ◽  
Allylic Alcohol ◽  
Marine Natural Product ◽  
Allylic Alkylation ◽  
Synthetic Studies ◽  
Key Steps

Synthesis of the fully functionalized macrolactone core of the highly cytotoxic marine natural product callyspongiolide has been achievedviaaZ-selective intramolecular H–W–E reaction and allylic alkylation of an activatedZ-allylic alcoholviaan SN2′ fashion as key steps.

Synthesis of Multi-Substituted Bicycloalkyl Boronates: An Intramolecular Coupling Approach to Alkyl Bioisosteres

2021 ◽  
Author(s):  
Yangyang Yang ◽  
Jet Tsien ◽  
Jonathan Hughes ◽  
Byron Peters ◽  
Rohan Merchant ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Material Chemistry ◽  
Novel Approach ◽  
Coupling Approach ◽  
New Type ◽  
Strain Release ◽  
Synthetic Studies ◽  
Bicyclic Molecules

<p>Bicyclic hydrocarbons, bicyclo[1.1.1]pentanes (BCPs) in particular, play an emerging role as saturated bioisosteres in pharmaceutical, agrochemical, and material chemistry. Taking advantage of strain release strategies, prior synthetic studies have featured the synthesis of bridgehead-substituted (C1, C3) BCPs from [1.1.1]propellane. This work describes a novel approach to accessing multi-substituted BCPs via a new type of intramolecular cyclization. In addition to the C1, C3-disubstituted BCPs, this method also enables the construction of yet underexplored tri-substituted (C1, C2 and C3) BCPs from readily accessible cyclobutanones. The broad generality of this cyclization is examined through synthesis of a variety of caged bicyclic molecules, ranging from [1.1.1] to [3.2.1] scaffolds. The modularity afforded by the pendant bridgehead Bpin resulted from the cyclization is demonstrated via several downstream functionalizations, highlighting the ability of this approach for programmed and divergent synthesis of multi-substituted bicyclic hydrocarbons.<br></p>

Sign in / Sign up

Export Citation Format

Share Document