Asymmetric Formal Synthesis of Trichodermamides B and C

Synlett ◽  
2021 ◽  
Author(s):  
Atsushi Kimishima ◽  
Masayoshi Arai ◽  
Hayato Saito ◽  
Violeta Petrova
Keyword(s):  
Michael Reaction ◽  
Oxime Ether ◽  
Formal Synthesis ◽  
Palladium Catalyzed ◽  
Key Features

AbstractAn asymmetric formal synthesis of trichodermamides B and C was achieved in 15 steps based on a tyrosine ester chiral-pool approach. Key features of this synthesis include stereoselective construction of a cis-1,2-oxazadecaline core by an acid-mediated tandem deprotection–intramolecular oxy-Michael reaction, oxime ether formation via an N-bromination–elimination sequence, and diene construction by a palladium-catalyzed demonomethylcarbonation.

ChemInform Abstract: Stereoselective β-C-Glycosylation by a Palladium-Catalyzed Decarboxylative Allylation: Formal Synthesis of Aspergillide A.

ChemInform ◽  
2013 ◽  
Vol 44 (40) ◽  
pp. no-no
Author(s):  
Jing Zeng ◽  
Jimei Ma ◽  
Shaohua Xiang ◽  
Shuting Cai ◽  
Xue-Wei Liu
Keyword(s):  
Formal Synthesis ◽  
Palladium Catalyzed ◽  
Decarboxylative Allylation

ChemInform Abstract: Formal Synthesis of Nitidine Through Palladium-Catalyzed Isocoumarin Synthesis.

ChemInform ◽  
2010 ◽  
Vol 27 (15) ◽  
pp. no-no
Author(s):  
T. MINAMI ◽  
A. NISHIMOTO ◽  
M. HANAOKA
Keyword(s):  
Formal Synthesis ◽  
Palladium Catalyzed

scholarly journals Catalytic asymmetric formal synthesis of beraprost

2015 ◽  
Vol 11 ◽  
pp. 2654-2660 ◽  
Author(s):  
Yusuke Kobayashi ◽  
Ryuta Kuramoto ◽  
Yoshiji Takemoto
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Subsequent Reduction ◽  
Formal Synthesis ◽  
Michael Adduct ◽  
Catalytic Asymmetric Synthesis ◽  
Weinreb Amide ◽  
Tricyclic Core ◽  
Catalytic Asymmetric

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α,β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C–C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C–H insertion and the subsequent reduction from the convex face.

Development of radical addition–cyclization–elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Tetrahedron ◽  
2007 ◽  
Vol 63 (40) ◽  
pp. 10092-10117 ◽  
Author(s):  
Okiko Miyata ◽  
Atsushi Shirai ◽  
Shintaro Yoshino ◽  
Toshiki Nakabayashi ◽  
Yoshifumi Takeda ◽  
...  
Keyword(s):  
Radical Addition ◽  
Elimination Reaction ◽  
Oxime Ether ◽  
Formal Synthesis

ChemInform Abstract: Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine.

ChemInform ◽  
2010 ◽  
Vol 26 (30) ◽  
pp. no-no
Author(s):  
F. GUILLIER ◽  
F. NIVOLIERS ◽  
A. GODARD ◽  
F. MARSAIS ◽  
G. QUEGUINER ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Formal Synthesis ◽  
Marine Alkaloid ◽  
Palladium Catalyzed ◽  
Coupling Strategies

Approach to the Core Structure of 15-epi-Exiguolide

Synthesis ◽  
2018 ◽  
Vol 50 (16) ◽  
pp. 3131-3145 ◽  
Author(s):  
Martin Maier ◽  
Alexander Riefert
Keyword(s):  
Michael Reaction ◽  
Chain Extension ◽  
Reductive Cyclization ◽  
Unsaturated Ester ◽  
Pyran Ring ◽  
The Core ◽  
Synthetic Strategy ◽  
Propargylic Alcohol ◽  
Key Features ◽  
Thermal Decarboxylation

The synthesis of seco acid 41 of the macrolactone part of 15-epi-exiguolide, containing a bis-pyran subunit and a trans double bond, is described. Key features of the synthetic strategy include a Feringa–Minnaard asymmetric organocuprate addition to unsaturated ester 17 to set the stereocenter at C15. The derived acid 8 (C9–C16 fragment) was ideally suited for combination with aldehyde 9 (C17–C21 fragment) via an aldol strategy leading to β-lactone 25 which upon thermal decarboxylation provided alkene 26. Chain extension led to propargylic alcohol 7. Treatment of 7 with a LAu+ catalyst promoted a Meyer–Schuster rearrangement to enone 30 that led to cis-tetrahydropyran 31 via intramolecular oxa-Michael reaction. The second pyran ring was prepared from alkoxy ketone 5 by reductive cyclization. The further steps toward macrolactone 43 were hampered by the epimeric mixture at C5.

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