Total Synthesis of 7,11-Cyclobotryococca-5,12,26-triene Using an Oxidative Radical Cyclization as a Key Step

2010 ◽  
Vol 12 (12) ◽  
pp. 2738-2741 ◽  
Author(s):  
Justin J. Davies ◽  
Thomas M. Krulle ◽  
Jonathan W. Burton
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Radical Cyclization

Biomimetic total synthesis of (±)-yezo'otogirin A

2014 ◽  
Vol 12 (16) ◽  
pp. 2519-2522 ◽  
Author(s):  
Hiu C. Lam ◽  
Kevin K. W. Kuan ◽  
Jonathan H. George
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Radical Cyclization ◽  
Biosynthetic Precursor ◽  
Oxidative Radical Cyclization

A concise total synthesis of (±)-yezo'otogirin A has been achieved via its presumed biosynthetic precursor using a late-stage biomimetic oxidative radical cyclization.

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

Synthesis ◽  
2020 ◽  
Author(s):  
Luis D. Miranda ◽  
Jazmín García-Ramírez
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Oxidative Cyclization ◽  
Dicumyl Peroxide ◽  
Cyclization Process ◽  
Radical Cascade ◽  
Oxidative Radical Cyclization

AbstractAn efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N-3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

ChemInform Abstract: Total Synthesis of (-)-γ-Lycorane Using Diastereoselective 5-endo-trig Radical Cyclization of N-Vinylic α-Halo Amides.

ChemInform ◽  
2010 ◽  
Vol 30 (13) ◽  
pp. no-no
Author(s):  
Masazumi Ikeda ◽  
Shinji Ohtani ◽  
Tatsunori Sato ◽  
Hiroyuki Ishibashi
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization

scholarly journals Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

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.

ChemInform Abstract: TOTAL SYNTHESIS OF SATIVENE AND COPACAMPHENE VIA A FREE RADICAL CYCLIZATION

1977 ◽  
Vol 8 (2) ◽  
pp. no-no
Author(s):  
P. BAKUZIS ◽  
O. O. S. CAMPOS ◽  
M. L. F. BAKUZIS
Keyword(s):  
Free Radical ◽  
Total Synthesis ◽  
Radical Cyclization

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

Total synthesis of (±)-acoradiene via radical cyclization

Tetrahedron ◽  
1993 ◽  
Vol 49 (45) ◽  
pp. 10263-10270 ◽  
Author(s):  
Yao-Jung Chen ◽  
Wen-Yuan Lin
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization

Total Synthesis of (±)-Euryfuran Through Ti(III) Catalyzed Radical Cyclization

2007 ◽  
Vol 4 (8) ◽  
pp. 553-555 ◽  
Author(s):  
Antonio Rosales ◽  
Cristobal Lopez-Sanchez ◽  
Miriam Alvarez-Corral ◽  
Manuel Muooz-Dorado ◽  
Ignacio Rodriguez-Garcia
Keyword(s):  
Total Synthesis ◽  
Radical Cyclization
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