Synthetic Studies on Podophyllum Lignans: Tributyltin Hydride-induced Radical Cyclization and Intramolecular Heck Reaction of a-Benzylidene-b-(o-bromobenzyl)-g-lactones

Heterocycles ◽  
1991 ◽  
Vol 32 (7) ◽  
pp. 1279 ◽  
Author(s):  
Masazumi Ikeda ◽  
Hiroyuki Ishibashi ◽  
Katsuhiro Ito ◽  
Masayo Tabuchi ◽  
Masazumi Ikeda
Keyword(s):  
Heck Reaction ◽  
Radical Cyclization ◽  
Tributyltin Hydride ◽  
Synthetic Studies ◽  
Intramolecular Heck Reaction

Bioinspired Total Synthesis of Marine Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A

Synlett ◽  
2021 ◽  
Author(s):  
Zhaoyong Lu ◽  
Chuanke Chong
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Recent Progress ◽  
Benzyl Bromide ◽  
Radical Cyclization ◽  
Ethoxy Group ◽  
Anti Cancer ◽  
Structure Revision ◽  
A Site ◽  
Intramolecular Heck Reaction

Our recent progress on the total synthesis of marine anti-cancer sesquiterpene quinone/hydroquinone dysideanone B and dysiherbol A was briefly highlighted. This success relied on some key transformations. The union of the terpene and quinone/hydroquinone moieties was realized through a site and stereoselective α-position alkylation of Wieland–Miescher ketone derivative with a bulky benzyl bromide. The 6/6/6/6-tetracycle of dysideanone B was constructed using an intramolecular radical cyclization and the 6/6/5/6-fused core structure of dysiherbol A was forged by an intramolecular Heck reaction, respectively. The possible origin of ethoxy group in dysideanone B was revealed by mimicking the isolation conditions at a late-stage. The structure of dysiherbol A was revised through the total synthesis of this natural product. Schmalz’s synthesis of dysiherbol A was also included.

scholarly journals Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3477 ◽  
Author(s):  
Mary Endoma-Arias ◽  
Helen Dela Paz ◽  
Tomas Hudlicky
Keyword(s):  
Total Synthesis ◽  
Spectral Data ◽  
Heck Reaction ◽  
Recombinant Strain ◽  
Radical Cyclization ◽  
Benzylic Alcohol ◽  
Phenethyl Acetate ◽  
New Compounds ◽  
Intramolecular Heck Reaction ◽  
Absolute Stereochemistry

The total synthesis of (+)-10-keto-oxycodone was attained from phenethyl acetate in a stereoselective manner. Absolute stereochemistry was established via enzymatic dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) that furnished the corresponding cis-cyclohexadienediol whose configuration corresponds to the absolute stereochemistry of the ring C of (+)-10-keto-oxycodone. Intramolecular Heck reaction was utilized to establish the quaternary carbon at C-13, along with the dibenzodihydrofuran functionality. The C-14 hydroxyl and C-10 ketone were installed via SmI2-mediated radical cyclization, and oxidation of a benzylic alcohol (obtained from an intermediate nitrate azide), respectively. The synthesis of (+)-10-keto-oxycodone was completed in a total of 14 operations (21 steps) and an overall yield of ~2%. Experimental and spectral data are provided for key intermediates and new compounds.

scholarly journals Approaches to the Cephalotaxine Skeleton Using an Intramolecular Heck Reaction.

1998 ◽  
Vol 46 (7) ◽  
pp. 1084-1089 ◽  
Author(s):  
Masazumi IKEDA ◽  
Ken-ichi HIROSE ◽  
Serry A.A. EL BIALY ◽  
Tatsunori SATO ◽  
Takayuki YAKURA ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Intramolecular Heck Reaction

First total synthesis of antihypertensive natural products S-(+)-XJP and R-(−)-XJP

2014 ◽  
Vol 12 (37) ◽  
pp. 7338-7344 ◽  
Author(s):  
Chaolei Wang ◽  
Guoxiang Wei ◽  
Xue Yang ◽  
Hequan Yao ◽  
Jieyun Jiang ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Heck Reaction ◽  
Intramolecular Heck Reaction

The first total synthesis of S-(+)-XJP and R-(−)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.

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